Summer of Love: Chipmunk Style
by Weirdfan5544
Summary: The Chipmunks and Chipettes spend the summer all alone doing things they really shouldn't be doing but want to anyway. Contains all the pairings and lemons.
1. Early Arousal Chapter 1

" _Theo Pleeeeeease!" She pleaded as Theodore continued to circle around her clit with his fingers touching it for only the briefest time. His cock pressed underneath her, spreading her folds around it. Eleanor bucked and grinded herself against him, desperate to get him inside her. God, she was wet!_

" _No, not yet," Theodore responded sharply with a smack to her ass before he continued to tease her, whispering in her ear from behind. "I don't think you're ready yet." He said stretching out her torturous pleasure, his other hand roughly squeezing her breast. "I don't know if you really want it."_

" _I do! I really, really do Theo! It's all I want! Please, just TAK_ _E ME!" she screamed at her lover begging him. At last, she felt him prodding at her entrance, she was finally about to feel him inside her. She felt herself stretching open…_

Suddenly Eleanor was startled awake by her 8 o'clock alarm, yawning she proceeded to slam her paw on the button turning it off. Burying her head in her pillow she groaned in frustration. ' _Another failed wet dream, how does that even happen?'_ She thought to herself. Sighing she pulled out her dream journal, detailing everything she could remember about her dream. What she had done, what Theodore had done, and what she wanted more of in the next dream. Plus what she wanted in real life.

It wasn't as though they hadn't done anything, but why did **she** have to instigate it every time? Eleanor loved the feeling of Theodore's paws grabbing her ass, squeezing her tits, or pulling her against him. But he never did so on his own initiative, she always had to put his paws where she wanted them. To guide him where he should be. To show him where to grab her.

' _Just once I'd like him to initiate, to kiss me first, to explore my body the way I want to explore his.'_ Eleanor wrote in her journal. _'To feel him slip his paws under my skirt, past my panties, to feel him grab me and bend me over while he fucks me hard and rough. I don't even care where it even is, I just want him to take me.'_

"That's enough." She said aloud. Going to close her journal her eyes fell on the last dirty dream she had, the one involving her sisters. The one where she had Jeanette between her legs and herself between Brittany's lapping away as...

"Snap out of it Eleanor." She said to herself closing her journal for real this time before getting up. Deciding not to change out of the shirt she had slept in she walked out of her room hearing the shower running, based on the noises coming out of the bathroom it was probably Brittany. Shrugging her shoulders Eleanor walked downstairs and began making breakfast.

She didn't do it every day, but she felt like making a big breakfast this morning. While getting the girdle ready for the bacon, Miss Miller walked into the kitchen.

"Ohhhhh, it's terrible, just terrible!" She wailed. Before Eleanor could ask what was wrong, MissMiller continued. "Fanny-Anne, you remember her, don't you? Well, it seems she fell and broke her hip. I told her I would come help her until she was all healed up, so I'll be gone for a good few weeks girls. Don't get into trouble!" Miss Miller rambled not noticing Eleanor was the only one present as she gathered up her luggage.

"Okaayyy then. Bye." Eleanor said a bit confused. She and her sisters had moved in with Miss Miller a few years back when their privacy became a bigger concern than sleeping in the same room. Still, they had grown to having Miss Miller around, it wouldn't be the same around here without her. _'Might be a bit more organized though.'_ She thought grinning at Miss Miller's trademarked absentmindedness while preheating the oven.

She was still making breakfast when the front door opened again. "Did you forget something, Miss Miller?" Eleanor asked without looking.

"N.. No, di.. did she go somewhere?" Simon stammered behind her. Looking behind her, Eleanor saw a slightly red-faced Simon nervously pushing his glasses back into place carrying a medium sized package under his arm.

"Yeah, apparently an old friend got hurt and she's going to help her recover. Is something wrong Simon?" Eleanor asked

"NO! I mean, no I'm fine. Why do you ask? I have a present for Jeanette." He stuttered shuffling from one foot to the other.

"Okay, well she's out on her morning walk so she'll probably be a while," Eleanor said confused at Simon's strange behavior.

"Okay," Simon said nervously. "Okay. I'm going to go put this in her room." He declared while going up the stairs.

"Well, that was weird," Eleanor said to the empty air as Simon walked out of sight. _'I wonder what he got her as a_ _present?'_ she wondered. Bending over Eleanor put a tray of raisin muffins in the oven.

' _Hmf, maybe Simon is scared he put something in Jeanette's oven.'_ She giggled to herself before sighing. _'At least that's not something I need to worry about when Theodore's showing no interest. Still isn't worth not being in his interest though.'_ She thought dejectedly.

Eleanor's phone buzzed unexpectedly with a text from Theodore.

 **Hey Ellie, I just wanted to make sure we were still good for the picnic tonight. You made your cheesecake, right?**

Eleanor's stomach dropped in guilt, she had completely forgotten about the picnic cheesecake when she went to bed the night before. It was an all-day event and she had promised to help referee the preschool Tee ball tournament that afternoon. A quick look at the clock showed it was already almost 8:30 and the first game started at 11. _'Crap.'_ She thought, she couldn't bear to let the little kids down.

 **I'm so sorry Theo. I completely forgot about it, and I have plans today. I can still do the Picnic, but I can't make the cheesecake in time.**

While waiting for a reply she felt terrible for forgetting it, she knew Theodore loved her cheesecake. As she thought of ways to repay him her dreams from the night before began to fill her thoughts. _'Maybe I could actually let him get past second base tonight. Maybe even…'_

Her thoughts were cut off with a new reply.

 **That's fine Ellie, it happens to everyone. How about I make the Cheesecake then? You keep the recipe in your cooking journal in your room, right?**

' _That's my Theo.'_ Eleanor smiled to herself happily. _'Quick to forgive and quicker to help.'_ Replying to Theodore in agreement she heard Simon run down the stairs far too quickly before stopping in the doorway. Turning to look at him she saw his glasses were askew, his breathing was heavy, his face was redder than Alvin's shirt and his jeans were noticeably tented.

Sighing a bit Eleanor turned to face him. "Let me guess, Brittany decided to walk naked down the hall again? I'm sorry, she's been doing that lately." She apologized. _'Not that you mind all that much_.' A small voice said in the back of her head _. 'Brittany has a great body.'_

Looking up at her Simon gaped like a fish before turning even redder and running out the door. Sighing, Eleanor called to her sister upstairs. "Brittany! I made Breakfast!"

* * *

' _I_ _can't believe I'm going to do this.'_ Simon thought to himself. It had been a little over a month since he had found Jeanette's secret on her laptop. A whole month of constantly thinking about his project and working on it. Not to mention worrying about how Jeanette was going to react when he finally revealed it to her. A look at his room's wall clock showed it was past 8. He knew Jeanette usually went on a walk at 7:30 and would be back around 9.

It had been an honest accident that he found out at all. He really was only looking for her notes on their science project when he borrowed her computer. What he found instead shocked more than he could have imagined and aroused him more than he thought possible.

Page after page of female chastity belts and erotica regarding the fetish. Simon would never have believed Jeanette could be such a fetishist, but he could hardly judge her on that count. _'How many times have I thought of having Brittany or Eleanor with us? Or even just them? Sometimes even Alvin or Theodore'_ Simon thought to himself.

While initially quite surprised Simon had to admit that some of Jeanette's more unusual sexual behaviors were very well explained by the revelation. Her immense enjoyment of fellatio for example, and to a lesser extent, her distaste for cunnilingus, as well as her claims of disliking pleasuring herself.

After finding out Jeanette's secret, Simon had begun his own research. Between his private 3D printer, careful examination of the various styles of belts and attachments, and study of chipmunk anatomy, he had done it. Simon had created not only a belt for Jeanette but a small vibrating anal plug as well as a small dildo modeled after Simon's own member. It wasn't as though he had access to views of many others of course, although he did make it slightly smaller to be as comfortable for Jeanette as it could be. Both could be inserted through the chastity belt and locked into place.

Simon couldn't stop imagining Jeanette in his invention, and only it. His thoughts drifted to what he would have her do if she agreed. _'Perhaps I'll have her beg? Or maybe bring her right to the edge of her orgasm before stopping the toys? Or should I lose all inhibitions and just have her rim me?'_ He thought lustily.

Packing his "present" for Jeanette into a box along with the note he had written for her and a small bottle of lube, Simon left his room and began his trip to the girl's house careful to ensure all his experiments were inert and safety precautions employed. A little over a year earlier Simon had accidentally left a chemical hotplate running and caused a runaway fire that had consumed the Seville house. Luckily no one had been home and Dave had purchased incredible insurance, though expecting Alvin to cause the damage, who still hadn't let Simon live it down.

Turning to the walkway to Miss Miller's house Simon saw her leave the house heading towards her car muttering something. He immediately hid behind the tree fearing for his life considering Miss Miller's driving. Only after she had turned the corner did he feel safe enough to come out.

Opening the door to the Chippettes house he was greeted by the gorgeous sight of Eleanor's ass outlined by her slightly too tight panties and slightly too short shirt. Her panties were a pale yellow and hugged her well-endowed cheeks showing every curve of her rear. Her white nightshirt came down to just past her hips, but her tail kept it from fully covering Simon's view.

Blood had long since rushed to his cock, but as he realized she had asked him a question much of it came back only to show his blushing. Stammering his way past Eleanor's questions he began to flee up the stairs. Looking behind him, he saw Eleanor bent over and stretched the material even further, showing much of her pale butt cheeks. _'Theodore is a lucky munk.'_ He thought to himself. _'I wonder how far they've gone together? I wonder what they're even into?'_ Simon couldn't help but imagine how Eleanor would look naked. How great the view would have been if she hadn't been wearing panties this morning. He knew she chose to go commando when she was required to wear tight clothing, she had said as much when she had done ballet.

Walking past the bathroom he heard the shower turn off, presumably by Brittany, and a small part of him briefly wondered what would happen if chanced a look. _'Probably a black eye, if I'm lucky. And then Jeanette almost certainly won't even consider wearing the belt tonight. Not that I would ever actually do it'_ He reassured himself.

Walking into Jeanette's room he couldn't help the fantasies that dance through his head. The ones about the girls he knew were natural, if the ones where they interacted weren't, but it was the ones about his brothers he wasn't so sure about. Pushing himself into Theodore, or feeling Alvin pushing into him.

About a month earlier Simon had accidentally walked into the bathroom as Alvin was changing and saw his cock. Simon would never admit to anyone, and tried not to even to himself, that his first thought was how would it feel inside him?

Simon knew self-exploration was healthy and natural, the rebuilt house with its individual rooms had allowed him to "explore" to his heart's content at night. It hadn't taken him long to realize he enjoyed anal stimulation. The majority of the time he had imagined it as anilingus performed on him. But ever since seeing Alvin naked he had been toying with insertion…

' _Stop it Simon, get back home, rub one out, then focus on your day.'_ He thought to himself sternly. _'You still need to judge that science fair this afternoon.'_ Walking out of Jeanette's room Simon heard Brittany moan his name quietly.

Worried that she might have fallen and hurt herself on her hardwood floor he peeked in her door only to be paralyzed at the sight before him.

Brittany was on the bed, facing away from him towards her nightstand with her face planted on the mattress eyes shut tight. She was rocking herself back and forth on a bright pink vibrator, one hand underneath her rubbing her clit. The other was pumping a smaller blue toy in and out of her asshole.

"Alivinnn…" Brittany moaned "are going to let me get away with thinking about Simon right now?" she said forcefully shoving the smaller phallus in even harder "or are you going to punish me? Make sure I never think about him again?" It took Simon's brain several minutes to fully comprehend what he was seeing but when it did it hit him like a freight train. _'She's thinking about me?'_ Simon couldn't help slowly stroking himself over his jeans.

Simon could only watch in wonder as Brittany rode herself to what looked like a powerful orgasm. Realizing he would get much worse than a black eye if he was caught he left quickly, almost running down the stairs.

When he was back in the kitchen Eleanor saw him and sighed "Let me guess, Brittany decided to walk naked down the hall again? I'm sorry, she's been doing that lately." Putting her hand on her hips she only accentuated the problems caused by such a short shirt showing more skin around her hips and exposing more of her ample cleavage. Unable to bring himself to answer and unwilling to risk embarrassing himself further he simply ran out the door, hearing Eleanor call her sister as he left.

* * *

Brittany awoke to the sound of her sister Jeanette dropping her shampoo in the shower as she was getting out. _'Having the room closest to the bathroom was supposed to let me shower first every morning and not wake anyone else up, that's worked out greaaat'_ She thought to herself irritably. Rubbing the sleep out of her eyes Brittany turned towards her bedroom door which was slightly ajar and gasped quietly in surprise.

Through the door she saw Jeanette bending over at the waist to pick up the fallen shampoo bottle. She was wearing nothing more than a towel wrapped around her chest which did absolutely nothing to hide her modesty from this angle. Her tail stood straight up providing her balance and exposing her nether region to the fluorescent light of the bathroom. Her heart-shaped butt cheeks seemed to guide the eyes to her lower lips, spread ever so slightly revealing the bright pink underneath.

Brittany couldn't help herself from staring while Jeanette finished picking up the bottle and put it back on the shower shelf. Closing her eyes Brittany pretended to still be asleep when Jeanette turned around.

Waiting for Jeanette to walk back to her room, Brittany's paw went straight between her legs. _'Why was that so freaking hot?'_ She thought to herself. _'I wonder what it would feel like to sit on her… NO.'_

Forcing herself to stop touching herself Brittany turned away from the door and tried going back to sleep, it was still before 8 after all. But every time she closed her eyes she couldn't help thinking of Jeanette. Finally sighing in frustration, she got up and walked to the hallway closet in front of Jeanette's room to grab a towel when Jeanette opened her bedroom door.

Hearing her gasp, Brittany turned to look Jeanette in the eye. She noticed her sisters' eyes wandered low and stayed down longer than they needed to. "Enjoying the view?" Brittany teased. She had done this more than once, but this was the first time she was right in front of her one of her sisters, Brittany couldn't help the excitement that built up inside her.

"NO! I mean, of course not. You just, I was surprised that's all." Jeanette said nervously as her face turned bright red. "I'm going for my walk now." She said rushing past Brittany.

Sighing in relief Brittany grabbed her towel and walked to the bathroom. _'Enjoying the view? Are you trying to creep her out Britt?'_ She thought to herself while starting the shower. _'Whatever just try to think about other things. Like what Alvin might do tonight'_

It was Friday night and Alvin owed her big time after missing the last two. ' _So, what if one was because he was sick and the other was a karate tournament?'_ She thought to herself. Brittany had no idea what Alvin had planned but, while she would never admit it to him, his plans were almost always fun.

Brittany's hand sneaked its way back between her legs as she got in the shower. "Mmmnh, I wonder what he thinks about when he's in the shower?" She asked the wall in front of her. _'Does he think of me on my knees sucking his cock? Or maybe fucking me from behind while spanking me? Pulling my tail hard, slamming me against the wall while I moan his name.'_ She thought while sliding a finger in and out of her folds.

' _Maybe he doesn't imagine just me. Maybe sometimes he imagines my sisters too.'_ Brittany thought as lust filled her mind. ' _Making us worship his cock, me kissing him while I push Eleanor's head down on his cock while Jeanette licks away at me.'_

Brittany continued to pleasure herself, never quite bringing herself to orgasm until she heard Eleanor get up and go downstairs. "Crap, I wasn't exactly quiet, was I?" She said to herself and reluctantly removed her hand from her pussy.

Beginning to actually bathe herself she had just rinsed the last of the shampoo from her hair when she heard footsteps come up the stairs. Turning off the water she looked through the slightly open door and saw a blue shirt walk past. Seeing Simon's head turn slightly as he passed the door Brittany had a sudden thought. _'What would he do if I just walked out naked right now?'_ A part of her was tempted, she could just blame him for looking if she did it. _'But what if he didn't? What if he just took me right there?'_ She wondered to herself, clearly, she was still horny.

Wrapping a towel around herself she walked across the hall to her room, only lightly slipping on her hardwood floor. She picked up her phone and placed it on her nightstand after setting it to record. Brittany had done this only a few times before, but it had been incredibly hot every time, and now she wanted to mix it up a little.

Pulling a hot pink vibrator out of her drawer plus its smaller blue friend she immediately went to work. She had prepared herself plenty in the shower and the larger vibrator easily slipped inside her folds stretching her. Brittany moaned as it did so. She began to lightly ride the toy as she toyed with her clit. She whispered sexily at her phone "Oh Alvin, is this really all you want me to do? All you want to do to me? I want you Alvin, I want to be your bitch, I want you to put me in my place."

Brittany's memories drifted back to the first time she and Alvin had sex, only a few short months ago soon after they "officially" began dating. They had played plenty before that but never anything more than oral. "I remember the first time Alvin, you were so strong, so tough. I thought you were going to do everything you wanted to do to me. Then you stopped, why'd you stop Alvinnnn?" She moaned as she slowly worked her ass open with her fingers.

"Maybe your brother's more of a man than you are huh? Maybe he'll fuck me like a bitch I am? Maybe I'll let him take my ass and you can watch." She whispered at her phone. "I think he is, he's about to make me his bitch like you won't, Simonnnn!" She moaned the last word a bit louder than she meant too as she slipped the smaller blue dildo inside her ass. She was surprised by how much she meant what she was saying. She wanted Alvin more than anyone but the thought of Simon taking her, of dominating her was better than she had thought it would be.

"Alivinnn…" Brittany moaned "are going to let me get away with thinking about Simon right now?" she said forcefully shoving the smaller phallus in even harder "or are you going to punish me? Make sure I never think about him again?"

She slowly increased her pace before having an incredibly powerful orgasm. Hearing footsteps go down the stairs she idly thought in her afterglow _'Simon sure was in Jeanette's room for a long time.'_ Panting slightly, she picked up her phone and saved the video. She put it in a message to Alvin, lightly teasing herself while she did so. She kept her finger raised above the send button. She had done this many times before, videoed herself masturbating and idly thought of sending the video to Alvin to tease him. But she never did. _'I don't want him thinking I'm a slut or anything.'_ She thought to herself.

Soon though Brittany heard Eleanor's call to breakfast, coupled with a loud rumble in her stomach she turned quickly off her bed throwing her phone on her pillow and throwing on a pair of panties and a shirt before going downstairs, never noticing her phone was sending the video.


	2. Early Arousal Chapter 2

" _Say his name! Say who's fucking your brains out right now Jeanette!" Eleanor panted pulling her sister's head out from between her legs just enough for her to breathe._

 _Jeanette pants, her face covered in her sister's juices, "Theodore" she manages to gasp "I have Theodore's giant cock in my soaking wet pussy and it feels so gooooood!" she moans before Eleanor pulls her back to her place._

 _Theodore grins and smacks Jeanette's ass causing her to moan into her sister's pussy. "That's right, you're my slut Jeanette, just like Eleanor and I'm going to fuck you until you break!" He growls at her, pounding himself into her relishing her muffled squeals._

" _Actually Theodore, she's my slut" Theodore hears from next to his ear. Suddenly he feels the tip of a cock pressing against his hole. "Just. Like You" Simon grunts as he buries his length inside Theodore's ass. Moaning like a bitch in heat from the sudden intrusion Theodore shoots his load…_

Falling out of bed with a groan, Theodore feels himself cum inside his underwear as a result of his wet dream. _'Well, at least today is my laundry day.'_ He thought to himself. _'That was the first one that involved the girls and my brothers too, I wonder if that means anything?'_

Getting up Theodore looks at his alarm clock he saw it was just before 8:30. _'Didn't I have something to do today?'_ Theodore thinks while rubbing the sleep out of his eyes _'Oh yeah, the picnic!'_

Quickly grabbing his phone, he sent a quick text to his date for the picnic, Eleanor.

 **Hey Ellie, I just wanted to make sure we were still good for the picnic tonight. You made your cheesecake, right?**

Theodore loved his girlfriend's cheesecake, it was probably the only pastry item she could make better than him though she was certainly the better overall chef. He soon heard his phone buzz as Eleanor replied.

 **I'm so sorry Theo. I completely forgot about it, and I have plans today. I can still do the Picnic, but I can't make the cheesecake in time.**

' _That sucks'_ Theodore thought to himself. _'its not like her to forget about these things, I guess I can make one instead though.'_ He quickly replied.

 **That's fine Ellie, it happens to everyone. How about I make the Cheesecake then? You keep the recipe in your cooking journal in your room, right?**

Pushing Eleanor and the cheesecake out of his mind, Theodore began getting ready for his day, grabbing a towel he stripped down and went to the bathroom to start a shower. While letting the water wash over him his thoughts turned to his date tonight with Eleanor, and from there, how far they had gone sexually. _'We've gotten pretty handsy before, but I wish she would do more.'_ He thought dejectedly. _'But I can't just ask her that, If I did she would probably think I just wanted her for sex and I really don't. I just need to be patient. I'm sure she'll be comfortable enough at some point.'_

' _But sometimes, I just want to push her skirt up slide right in next to her panties and use her.'_ Theodore thought as he slowly stroked his cock. _'Push into her, make her moan my name, slap her butt until it's redder than Alvin's shirt'_ He thought as lust filled his mind slowly his thoughts turned back to his dream the night before as his hand reached back to prod at his puckered asshole.

' _And sometimes, I want Alvin or Simon to do the same to me. I would need to let them fuck me to let me use Brittany and Jeanette. It would be worth it though. To need to take them in the ass to take their girls.'_ Theodore slowly slid his middle finger into his hole all the way to the first knuckle, gasping as he heard a pounding knock on the door.

"Hurry up Theodore, you're not the only one who wants to take a shower this morning!" Alvin shouted from the hallway.

"Give me a minute Alvin, I'm almost done!" Theodore called back. _'I guess that's not happening this morning.'_ He thought to himself, finishing up his shower.

Walking out into the hallway with a towel wrapped around his waist Theodore saw his brother standing next to the bathroom door. "Jeeze Theo, what took so long? Thinking about Eleanor again?" Alvin teased.

"N.. No I wasn't, I was just taking a shower." Theodore responded embarrassed.

"Uh huh, you were just standing in the shower for over 20 minutes just enjoying it?" Alvin asked sarcastically. "Yeah sure, I believe that, especially with that tent you're pitching there Theo." Alvin said pointing at Theodore's crotch.

Yelping in embarrassment Theodore ran into his room hearing his brother laugh behind him before he called out. "By the way, send Brittany a text for what we need for groceries since Dave's out of town setting up our tour, it's her turn to get them today."

Theodore slammed the door shut behind him, slightly irritated at Alvin's behavior, especially because he clearly did have an erection. _'Its even worse when he's right.'_ He thought to himself. Sighing he looked at his phone and began sending Brittany the list he needed before getting dressed.

Theodore walked into the hallway when he heard someone running up the stairs, turning to face them he saw Simon red-faced from exhaustion run into his room and slam the door shut. _'What's that about?'_ He wondered to himself. Going over to his door and hearing the noises coming out of his brother's room Theodore's face turned bright red. "Oh" He whispered in realization before backing away and walking downstairs.

Pouring himself a bowl of cereal he was eating when Alvin came down the stairs dressed far nicer than he usually did. "I'm heading into the city to talk to the publisher about our last album." He said seeing Theodore's questioning look. "Dave asked me to last night, I'll be home in a few hours."

"Well I won't be making dinner tonight." Theodore responded. "Eleanor and I have a picnic tonight."

"Ohh so you were thinking about tonight in the shower?" Alvin teased once again causing Theodore to choke. "And anyway, that's fine, I'm pretty sure all of us have a date tonight. Brittany will kill me if I don't do anything with her a third Friday in a row. Anyway, see you later." He said walking out the door before his younger brother could recover.

"Alvin." Theodore groaned irritably after his coughing fit was over. Finishing his breakfast, he walked over to the girls' house just as Brittany and Eleanor were about to leave.

Hey Theo." Eleanor said as he walked in kissing him on the cheek. "Sorry again for forgetting the cheesecake, I already got everything out you'll need, and my journal is on my desk."

"That's fine Ellie I don't mind making it." He replied happily "Hey Brittany, did you get my text with the groceries?"

"Yeah Yeah I did, I was going to drop Eleanor off and then go get them, did you need to add anything before I left?" Brittany replied. "Oh, by the way, Jeanette's in the shower so don't be surprised if you hear someone upstairs."

"No, I just wanted to be sure, bye." Theodore responded as they left. Walking upstairs he went into Eleanor's room and looked around. "Now where's her cooking journal, she said on her desk." His eyes soon settled on the journal in the middle of her desk that had a bookmark sticking out. "This must be it, she even marked the page for me." Theodore said before opening the book to the marked page.

Reading the first few sentences Theodore's mouth dropped open in shock. _'This is not her cooking journal.'_ He thought but he couldn't stop reading. Soon a tent was forming in his pants as he read more and more of Eleanor's dream journal's most recent entry. _'It could almost be word for word one of my dreams, is this really what she wants?'_ Theodore thought to himself in confusion. _'I didn't want to hurt her, or push her too far, but she wants me too?'_

Slamming the book shut he immediately felt guilty. _'Those are her private thoughts.'_ He thought to himself in shame. He soon found the right book and left Eleanor's room, but not with one last look at her journal, sitting on her desk.

* * *

Jeanette finished getting dressed for her early morning walk. She liked to take these walks because it gave her a chance to think and get ready for her day. It also let her make sure she got to shower before Brittany used up all the hot water.

Jeanette swung open her door to the gorgeous sight of her sister Brittany's naked body. Her eyes quickly examined every inch of Brittany's skin. Her thin waist appeared to guide the eyes up to her pert breasts, or down to the folds of her lower lips. Jeanette couldn't bring herself to look away before she heard the sarcastic voice of her sister.

"Enjoying the view?" Brittany teased. She had done this more than once, but this was the first time Jeanette had been close enough to make out every detail.

Jeanette felt her cheeks burn in embarrassment as she realized she was still standing "NO! I mean, of course not. You just, I was surprised that's all." She heard herself stammer out. "I'm going for my walk now." She said rushing past Brittany.

' _Smooth Jeanette,'_ She thought to herself as she left through the front door. _'why don't you just go back and ask if you can share a shower and give her a tongue bath? Can't be any more awkward than that was.'_

Slowly the idea takes hold in Jeanette's mind. On her knees between her sister's thighs, lapping away at her pussy, feeling her sister's hands in her hair grinding against her face moaning _"good girl Jeanette, lick my clit, that's it, ohhhh"_

"Snap out of it Jeanette!" She says to herself as she's barely turned the corner of their street. Shaking her head, she tries to focus on her walk. But her thoughts kept drifting back to her sister's body for the entire time.

Finally, she makes it back to her house and walks through the door. Smelling the air, she feels her stomach rumble at the smell of bacon, eggs, and muffins. Going into the kitchen she grabs a plate and scoops some bacon and eggs on to her plate and grabs a muffin before sitting down to eat at the table. Soon after she sits down Brittany walks back into the kitchen and sees her.

"Your back early, did you need anything from the store? It's my day to shop for groceries." Brittany asks nonchalantly.

Deciding to just pretend nothing had happened Jeanette said "No, I can't think of anything." Feeling a slight blush fill her cheeks as she thought of that morning.

At that moment Eleanor walked into the kitchen "Oh Jeanette you're back already?" She said in greeting. "Simon left you a present in your room."

"He did?" Jeanette asked bewildered. Her birthday wasn't for a few weeks at least and they hadn't even been dating that long to be any kind of an anniversary.

"Yeah, looked pretty big too, my bet is its some kind of invention." Eleanor said. "Anyway, Theodore is going to be over today making a cheesecake I forgot to last night, just to warn you."

Finishing up her breakfast Jeanette went to the stairs telling her sister's "It was hotter than I thought it would be this morning, so I'm going to go take a shower."

"Was it? Good to know, just remember to be fast, all three of us have showered this morning so you don't have that much hot water left." Brittany said smirking at Jeanette.

Not having a response to that wouldn't lead to more embarrassment, Jeanette quickly went upstairs and started the shower. Soon she was clean, just as the water lost its heat. Wrapping a towel around herself she walked to her room and shut the door. She saw the package Simon had left for her on her bed with a letter on top of it.

Opening the letter, she began to read.

' _Jeanette, I want to preface this letter by saying that no matter what you choose, no matter what you decide, it won't change my view of you. You are incredibly intelligent, amazingly beautiful, and astonishingly kind. In short, I can think of no one closer to perfect for me than you.'_

 _'When we were working on our science project, I needed you notes one night. Searching your computer for them I stumbled across your… private albums. I saw it all Jeanette. All the belts and cages, all the pictures and stories. It was something I had never expected to find on your computer.'_

 _'It was the most arousing thing I had ever seen. For weeks now, the idea of you in such a belt has been dancing in my head. For weeks now, I have been working on a belt for you, and I finally finished one, along with a few accessories.'_

 _'In the box, you will find the belt, the key, and the toys, all you need to do is put it on and insert the toys through the holes and push the button on the bottom. Once that's done they can only be removed with the belt.'_

' _If you decide to wear it, give me the key tonight when I pick you up for the science exhibit. If not, know that it won't change my view of you.'_

 _Yours truly, Simon._

Jeanette's sheets were wet, and not only from the water from her shower. _'Oh god, he found them, he found the files.'_ She thought in embarrassment. _'He found them, and he liked them?_

Slowly opening the box, she saw the belt Simon had written of. It looked like it was made of polymer plates with thick but lightweight cloth keeping them from touching her skin. It was made in the simple classic thong style, wrapping around her waist and between her legs with three holes built into it. A small pocket held a padlock that would lock a arm of the belt around her waist. It was sleek and would be difficult to notice in jeans or a dress and would easily be mistaken for normal underwear. Simon had clearly put effort into building it.

' _He really worked hard on this, and he wants me to wear it? Does he know what I really want? Did he read the stories? Of course he did, he's Simon.'_ Jeanette thought to herself while looking at the belt.

Slowly, Jeanette began to put the belt on. Sliding it up her legs, she fed her tail through the topmost hole. When it was finally completely around her waist she began to pull it tight until it was ready to be locked. It was snug, but not uncomfortably so. It also gave her no way to touch her clit from any angle. She was once again impressed with the craftmanship Simon had put into it.

Jeanette took the larger of the two toys in her hand. It was still fairly small, if she had to guess it was a little more than half the size of Simon's own member. There was a small bottle of lube in the box, but she knew she wouldn't need it. She slowly slid it inside the hole in the belt directly above her core, feeling it filling her up she let out a quiet moan. Finally, it was all the way in. Upon pressing the button on the very bottom, she felt it click into the plate. She couldn't get a grip on it at all and as such had no way to remove it.

Her attention then turned to the second toy in the box. It was far smaller, less than half the size of the first. It started out small at the tip before widening slowly until it sharply narrowed to just larger than the tip. This time Jeanette needed the lube, copiously cover the toy she pressed it against her rear, slowly applying force to push it in. she felt it stretching her entrance before it slammed around the base of the toy causing her to let out a quiet yelp. She soon pressed the button on the bottom of it as well and felt it lock into place.

Sliding the padlock through the hole Jeanette left it there for a moment. Her heart racing. _'Am I going to do this? Really do this?'_ She soon thought of the letter. _'He said the key was in the box, I'll be fine.'_ She thought before locking the padlock. That one simple motion caused a wave of pleasure to radiate from her core drawing out a small moan.

Jeanette had no idea how long she lay on her bed, her fingers dancing Idly over her belt, unfelt by the skin underneath. Thoughts and fantasies went through her head too fast to count. Eventually though her attention returned to the box and she looked inside for the key.

At first, she was confused because she saw no key, until her eyes fell on a small paper envelope. Picking it up she felt the key inside and raising it to the light she could see it clearly inside the envelope. The sealed envelope.

Jeanette felt like she was on the brink of orgasm from that alone. There was no way to remove the key without opening the envelope, and to open the envelope was to admit she opened her cage. Jeanette didn't know if it was Simon's way of challenging her, in fact she doubted it was, but almost without realizing it, she decided to meet the challenge it presented.

Setting the unopened envelope down on her dresser she threw on an old pair of jeans and a shirt. Laying down on her bed she picked out a book and began to read, doing her best to put the key, her date tonight, and the two toys currently inside her out of her mind. Because she knew if she didn't, they would drive her crazy.

It didn't help much.

* * *

Alvin woke up to the sound of birdsong. Rubbing the sleep out of his eyes he grumbled, a bird had decided to build her nest right outside his window, so he hadn't been able to sleep past nine for weeks now.

Getting up he saw that it wasn't much past 8:30 quickly getting out of bed he made sure his nice clothes were still nice and reviewed his argument for there album. A few years earlier, upset at Dave spending to much time on the Chipettes newest album to talk to a publisher who had pulled theirs, Alvin went to meet with them himself and had managed to secure them funding for a new album later.

Dave was maybe more than a little upset that Alvin had put a whole album's worth of songs on his schedule, but he had been pleased with the initiative Alvin had shown and had slowly introduced him to his side of the band. Now Alvin could do almost anything Dave could, he had even helped co-write a few songs. Though even Alvin admitted Dave was much better at the job than he was.

Still, the meeting tonight was simple enough. More of a confirmation thing than anything else so Alvin wasn't too worried. He still needed to look his best though, Dave's orders.

Walking to the bathroom he heard Theodore in the shower. Knocking on the door he called through the door "Hurry up Theodore, you're not the only one who wants to take a shower this morning!"

"Give me a minute Alvin, I'm almost done!" Theodore called back.

Walking out into the hallway with a towel wrapped around his waist Theodore looked at Alvin standing next to the bathroom door. "Jeeze Theo, what took so long? Thinking about Eleanor again?" Alvin teased.

"N.. No I wasn't, I was just taking a shower." Theodore responded embarrassed.

"Uh huh, you were just standing in the shower for over 20 minutes just enjoying it?" Alvin asked completely lying considering he hadn't been awake 20 minutes earlier. Suddenly noticing his brother's erection Alvin smirked

"Yeah sure, I believe that, especially with that tent you're pitching there Theo." Alvin said pointing at Theodore's crotch.

Yelping in embarrassment Theodore ran into his room hearing Alvin laugh behind him before a thought occurred to him. "By the way, send Brittany a text for what we need for groceries since Dave's out of town setting up our tour, it's her turn to get them today." He called out. Just before he slammed the door shut Theodore's towel fell away revealing his butt. Alvin couldn't help but look at it though the sound of the slamming door shocked him before it could really enter his thoughts.

Alvin showered quickly, his thoughts still on his meeting that day. When he was done he quickly got dressed and went downstairs seeing his brother eating breakfast. Theodore soon looked at him strangely given Alvin's good clothes.

"I'm heading into the city to talk to the publisher about our last album." He said seeing Theodore's questioning look. "Dave asked me to last night, I'll be home in a few hours."

"Well I won't be making dinner tonight." Theodore responded. "Eleanor and I have a picnic tonight."

"Ohh so you were thinking about tonight in the shower?" Alvin teased once again causing Theodore to choke. "And anyway, that's fine, I'm pretty sure all of us have a date tonight. Brittany will kill me if I don't do anything with her a third Friday in a row. Anyway, see you later." He said walking out the door before his younger brother could recover.

Walking out to his miniature car Alvin saw Eleanor and Brittany leave in Brittany's car. Alvin was soon on the road and on his way to he bus station as his car wasn't legal to drive on the highway. It wasn't until he was there that he realized he had left his cellphone at home. "Well that sucks." He said sullenly as he rode the bus into town with nothing to do. It was going to be a long few hours.

Several hours later Alvin pulled back into the driveway and walked inside. The meeting had gone about as he expected but all the waiting and both bus rides had been mind-numbingly boring without his phone. He soon found it on his nightstand right where he had left it the night before. Picking it up he saw he had a message from Brittany from that morning. _'Crap.'_ He thought to himself in a panic. _'It's probably her telling me exactly what she wants to do tonight, and I don't have the time to set anything up now. I'm so screwed, and probably not in the fun way.'_ Opening the message, Alvin saw it was a video. _'Okay that's weird, she never sends me a video.'_ When it had finally downloaded, Alvin pressed play.

The first few seconds was a close up of Brittany's face as she fumbled with the phone before backing up. Alvin's eyes nearly popped out of his head as he saw she was completely naked.

Brittany laid down on the bed facing the camera. Her face was hidden by both the bottom of her nightstand and her blanket, and her body was raised to high to really be seen. But it was still obvious what she was doing by the tone of her voice as she sexily whispered at her phone. "Oh Alvin, is this really all you want me to do? All you want to do to me? I want you Alvin, I want to be your bitch, I want you to put me in my place."

' _I.. She… What?!'_ Alvin thought in utter confusion, this expressed desire not meshing at all with the loud, willful, and confident girlfriend he knew. His cock was straining against his clothes before he opened his pants and let it out where it stood straight up.

"I remember the first time Alvin, you were so strong, so tough. I thought you were going to do everything you wanted to do to me. Then you stopped, why'd you stop Alvinnnn?" Brittany moaned in the video. Alvin remembered that night too, but he remembered it a bit differently than Brittany did. _'You said ow. I hurt you.'_ He thought to himself _'I practically threw you on the bed, you hit your head and I was scared. But god what I wanted to do to you, to have you do. What I still want to do.'_ Alvin thought lustily as he slowly stroked his cock.

"Maybe your brothers more of a man than you are huh? Maybe he'll fuck me like a bitch I am? Maybe I'll let him take my ass and you can watch." Brittany whispered in the video. "I think he is, he's about to make me his bitch like you won't, Simonnnn!"

At that moment, Alvin shot his load for two reasons, the first thought that ran through his head was _'She likes anal? Goddamn, I love her.'_ The second was the thought of fucking Simon's ass while he pounded Brittany's.

Recovering from his orgasm Alvin paid little attention to his thoughts about his brother, he had been having them for so long, about all of those he considered his siblings that he no longer cared about the supposed "wrongness" of them. He was in a relationship with Brittany and that was enough to keep him content. The fantasies would need to remain just that.

He soon noticed Simon in the background of the video. _'He must have heard her moan his name, I don't blame him for looking, or for stroking himself, his view must be way better than mine.'_ Sexy Brittany was, but the angle of the video was about as bad as it could be.

Alvin soon shut off the video and began to think about its implications. _'So, she likes being put in her place huh? I need to talk to her about it tonight.'_ Alvin began to giggle, and then laugh nearly uncontrollably.

' _I guess I will get screwed in the fun way.'_


	3. Date Night Chapter 1

"Are you okay Theodore? Is there something wrong with your food?" Eleanor asked her boyfriend. She was worried about Theodore. First, she had noticed that the cheesecake he made hadn't been up to par with his usual skill. Next, she had noticed he was unusually quiet compared to the chattering furball he typically was. The most obvious difference however, was his practically untouched food. He never acted this way unless he was sick or upset.

"I'm fine Ellie, just thinking," Theodore responded with an attempt at a smile that died before it could reach his eyes.

' _And now he's lying to me.'_ Eleanor thought to herself, her concern was only growing. Theodore was a terrible liar and he knew it. The only times he lied to her was when he thought it was important, which basically amounted to never. "Are you sure Theo? You know you can talk to me about anything, right?" Eleanor reached over and grabbed his hand in her own squeezing it lightly.

Theodore raised his eyes to meet Eleanor's. In them he saw only concern and affection. But in his mind, he could only imagine them wide in fear or arousal, he wasn't sure which. _'I can sure, but will you still be here tomorrow if I do?'_ He thought to himself. "I know Ellie, but not right now," Theodore said, trying to reassure her.

Eleanor scooched herself over to sit next to him, grabbing his arm she draped it around her as she lay her head on his shoulder. They had managed to get a spot at the park where the trees framed the setting sun almost making you feel like you were in a forest. Watching the pale orange disc sink beneath the horizon Eleanor became painfully aware of Theodore's hand alternating between tensing up as it touched her and relaxing laying back on her side, before tensing up once more. _'What is his problem?'_ Eleanor thought to herself in confusion. _'He not usually this fidgety around me.'_ Slightly irritated at her boyfriend's actions she took his hand and placed it firmly on the side of her thigh, right above her butt, just as the twilight fully engulfed them.

Theodore practically jumped to his feet at the same moment. "The sun's set, we should get home." He said almost angrily. Looking down he saw the hurt in Eleanor's eyes at his actions and tone. _'Smooth Theo.'_ He chastised himself ' _Don't want to hurt her, the best way to do that is to reject her! You dumb jerk.'_ Quickly he began to pack up the picnic and after a long moment, Eleanor did too. When she finally looked up, her eyes they flashed with anger.

"Well? Are you coming or what?" Eleanor demanded as she walked briskly down the hill towards their street. Hearing Theodore sigh behind her he soon followed carrying the picnic basket. Every step she took Eleanor fought to contain her frustration, and even worse, her tears. _'What is his problem?'_ She thought in irritation. _'I literally put his hand on my ass, and what does he do? Jumps up like I kicked him! Why? What happened to him? What's wrong with me?'_ Blinking quickly as her vision noticeably blurred.

It was a short walk back to her house. It looked like Jeanette and Brittany were still out with Simon and Alvin respectively. Holding the door open for Theo, Eleanor gestured to the kitchen table. "Just set it there." She said flatly. When he did Eleanor kept the door open. Theodore walked over to her while she refused to meet his eyes.

"Ellie I…" Theodore began _'What? I didn't mean to hurt you? I read your private journal? I want to bend you over that couch and make you scream my name?'_ He thought to himself. All were true, but he didn't know what to start with, or how.

"Oh don't you _Ellie_ me, Theodore!" She snapped at him meeting his eyes. "You don't get to call me that after what you just did! Especially not after _months_ of doing practically the exact same thing! I get it, you don't I'm attractive! Whatever, I don't care!" Eleanor shouted at him shrilly. Tears threatening to spill down her face

"What? Not attractive?" Theodore sputtered out in confusion. "Ellie, you're beautiful! I've told you that a million times! Where the hell did you get the idea, I didn't think you were attractive?"

"Oh, I don't know, maybe because you seem to do everything you can to avoid touching me?" Eleanor said mockingly. "Maybe because in the entire time we've known each other you haven't made a move on me one, single, goddamn time!" She shouted, tears running freely down her cheeks. _'Oh_ _great, now I'm crying.'_ Eleanor thought to herself.

"Before we started dating I couldn't wait for you to ask me out, but you never did," Eleanor stated. "So, I had to. Then I couldn't wait for our first kiss, but you never pushed, so I had too!" She grunted. "The first time we were alone, and I mean really alone not just in one of our rooms. I couldn't wait to feel your hands all over me, but you wouldn't touch me. SO I HAD TO!" Eleanor shouted, unleashing all her pent-up feelings. "Every. Single. Step of our relationship I have been the one to take the risk and there's only one reason I can think why that is and you just proved it tonight Theodore." Eleanor sobbed. "NOW GET OUT!"

Theodore bowed his head until his hair hid his eyes. Eleanor could hear him taking several deep breaths, as though he was trying to calm himself down and stop himself from crying. _'Good, he deserves it.'_ She thought to herself. Immediately a part of her felt horribly guilty, pushing all the weight of her frustration of the last few months on his shoulders all at once was hardly fair. But another part of her felt free, she had finally said the thoughts that had been threatening to boil over for weeks. "No." She heard Theodore speak in a calm, carefully measured voice.

Looking up Theodore saw the pain in Eleanor's eyes, the truth of her every accusation. Except for the last one. "I think you are the most beautiful girl I have ever laid eyes on Eleanor Miller. You are also the kindest, gentlest, sweetest, and most nurturing person I have ever met. I love you, and I have for a long time now." Opening her mouth to respond with what would probably be a snarky reply Eleanor had the wind knocked out of her when Theodore shoved her up against the wall and any protest she would have uttered was soon muffled as Theodore kissed her deeply, his tongue was exploring her mouth as he pressed against her. His left paw was squeezing her right breast roughly as his right slid its way past her skirt and began to rub between her lips through the fabric of her panties.

Theodore was hyper-aware of everything he was doing, waiting for the smallest sign that Eleanor didn't want this. _'I really hurt her, didn't I? It's almost funny, I didn't do any of that because I didn't want to hurt her and instead she took it the exact wrong way.'_ Theodore felt Eleanor relax and begin to return his kiss, letting out little moans and small whimpers as Theodore explored her body. His firm grip was causing her to melt against him.

Gasping for air when Theodore finally let her go Eleanor was stunned, her tears had stopped, all her body's moisture was suddenly needed elsewhere. "Theo…" she whispered breathlessly. _'Where did this come from?'_ Eleanor thought to herself in a lust filled haze. _'Where did Theo get these ideas? When did he figure it out?_

"Not here," Theodore growled. "I have been dreaming about this for years and it is not happening in the fucking hallway." He picked Eleanor up, literally sweeping her off her feet and carrying her bridal style towards the stairs to her room. _'I forgot how strong he is.'_ Eleanor thought to herself still not quite believing the turn of events. "I must be dreaming." She whispered to herself as Theodore opened the door to her room.

Suddenly Theodore threw her on her bed where she yelped in surprise. "No." he said, his voice deadly serious. This is real Eleanor. It better be" Theodore growled as he unbuckled his pants. "But your dreams did help me. They let me know that you wanted this just as much as I did. As much as I **do**. Now, show me." He demanded. Gazing at her with a look that brokered no debate.

Shivering in desire Eleanor obeyed, slowly removing her shirt, then her bra, followed shortly by her skirt and panties. At last, she lay before Theodore naked as the day she was born as he stood at the foot of her bed staring at her, drinking in the sight of her body. As she moved to cover herself he stopped her.

"No" Said Theodore. "I want to look." Slowly crawling on Eleanor's bed, he grabbed her arms and moved them away from her body. His erect cock stood out nearly perpendicular from his body and dragged lightly across her legs and thighs as Theodore lined his face up with her own causing Eleanor to moan.

At that moment Theodore kissed her once again, holding her down with one hand and using the other to toy with her entrance, slowly prodding it more and more open. Eleanor moaned in pleasure when he finally slipped a finger in.

Theodore was in heaven. He could feel every beat of Eleanor's heart as she writhed underneath him. He felt himself get harder as Eleanor tightened around his finger. Every gasp and moan was better than all the music he had ever heard and in that moment all he cared about was the girl beneath him and making her his own.

Pulling back, Theodore lifted Eleanor's legs up, pushing them apart as he lined his cock up with her entrance, pressing the tip against her causing them both to groan in pleasure. Looking Eleanor in the eye Theodore asked her the unspoken question. He could see the desire in her eyes. It was almost nothing, a slight bob of her head. Grinning, Theodore leaned over to Eleanor's ear and whispered. "How's this for making a move?" As he thrust himself forward, burying himself inside Eleanor causing her let out a high-pitched moan.

' _Oh god, he's inside me. Theodore is inside me. Theodore is fucking me!'_ Eleanor thought in ecstasy. Moaning even louder as Theodore pulled out and slid back in she was soon lost on a trance of pleasure. She had never felt so full before. She groaned as Theodore dug his claws into her legs, using them as leverage as he increased the power of his thrusts. Each one rocked her body, causing waves of pleasure to radiate from her core. Suddenly Theodore pulled her legs up even higher, causing each one of his thrusts to rub right against her G-spot.

The pleasure that had rocked her body previously now felt like shallow ripples compared to the waves that made her writhe as Theodore increased the speed and power of his thrusts. _'Oh god, he's going to break me!'_ Eleanor thought to herself in a lustful haze. "Oh yes Theodore, right there, fuck me like a bitch in heat, use me to make you cum." Eleanor began to babble as her climax threatened to overwhelm her. Theodore thrust inside her once last time, digging his claws in deep enough to draw blood he grunted. "Take this, I'm going to fill you up. Now CUM!"

Eleanor felt Theodore bury himself inside her core, she felt each and every spurt of his cock and it emptied his load, each one timed perfectly with a spasm, making her clamp down on him even harder. She gripped the sheets so tight she heard the fabric break under her claws. "Theodore!" Eleanor moaned in heaven sent ecstasy.

Theodore held her up until he had begun to soften. Slowly setting Eleanor's legs down he pulled out of her eliciting a small groan of disappointment from Eleanor. Panting, he looked down at the girl beneath him. Her eyes were shut tight, as though she was fighting to remember something. Her hair was a mess, wild and tangled all over. A light sheen of sweat covered her body from the strenuous lovemaking they had just done. From around her legs, he saw the ten small punctures he had made from his too hard grip. "You're beautiful," Theodore said, his normal gentle self returning.

' _It finally happened. I did it. We did it. I had sex with Theodore.'_ Eleanor thought to herself. She felt the sweat that covered her skin. She knew her hair was a mess and she felt the light pain from Theodore's claw marks. But it was the feeling of his seed she was focusing on, it was deep inside her, Eleanor was doing her best to keep it there. _'I must look like a real treat'_ She thought to herself sarcastically right before she heard Theodore's words. "Oh sure, of course I am, isn't it obvious?" She said mockingly.

Suddenly, Theodore was kissing her once again. But where before they had been hot and hard this one was sweet and gentle but sharing the same passion. "I'm serious Ellie, you are beautiful." He says as he breaks the kiss. "I meant every word I said back there. And I am so, so sorry that I hurt you. I was just scared of, well hurting you I guess." Theodore lies down next to her staring at the ceiling.

"Hurt me? Theodore, how did you think you were going to hurt me?" Eleanor asks bewildered. "You've done anything, ever, to make me seriously think you would hurt me deliberately."

Theodore doesn't respond for a long moment causing Eleanor to sit up, leaning on an arm to look at him. "I didn't want you to think I only wanted you for your body." He finally answers in a quiet voice.

Eleanor begins to giggle before losing control and descending into a fit of laughter. "It's not funny, I'm being serious." Theodore says indignantly. "I think you're an amazing person and I want to be with you for, well for as long as you'll be with me. I figured if I let you move at your own pace then…" Theodore was suddenly cut off as Eleanor kissed him. Surprised at first Theodore soon recovered and pulled her towards him.

Eleanor eventually broke off the kiss but kept a large grin on her face. "Theodore, there is a very large difference between wanting me for just my body and wanting my body. I want you to want my body." She laughed, emphasizing her point by rubbing her body on top of him. "And you better still want it in the morning because you're not off the hook yet, we have months of sex to catch up on because of you." Eleanor teased.

Theodore rolled them over causing Eleanor to be laying on her stomach with her ass facing Theodore. Her eyes widened in shock as she felt Theodore's manhood rubbing against her pussy again. He leaned down and whispered in her ear. "Why wait till morning?"

* * *

 _ **AN: Not gonna lie, this is my first proper lemon and I feel like it shows. This is also the chapter, at least of these first 5 or so, that I felt I had the least idea of what I wanted from and I feel like it shows. I also feel like it fails to convey a little bit of what I meant for it too. I also think it's too short. Put simply, I'm a little disappointed with this chapter.**_

 _ **That being said, I started with these two before and I felt like I should do so again. The next couple chapters should be a little bit longer and should flow a little nicer considering they are more my speed. I know I didn't say this before, but reviews and criticism are more than welcome. Hope you're enjoying the story so far and thanks for reading.**_


	4. Date Night Chapter 2

Simon checked his phone for what felt like the millionth time that afternoon. _'Still no text.'_ He thought uneasily. He had turned his phone off while judging the science fair, but he had yet to receive a message from Jeanette. That wasn't in and of unusual. Both of them tended to eschew texting in favor of phone calls when apart from each other and face to face conversation when at home. In addition, neither of them felt the need to constantly affirm their relationship with meaningless interaction.

Still, after the bombshell, he had dropped on her bed this morning Simon had expected _something_. He had feared an angry message calling him a dirty perverted pig at the worst, though he was confident that she was interested in it, he had expected some sort of message nonetheless. The absence of knowledge made him nervous. _'Has she even opened it? What if she hates it? Is she still considering it?'_ These thoughts and more danced in his head.

Sighing, Simon held his head in his hands. _'It's Jeanette.'_ He assured himself. _'She would understand being interested in… it. Even if she doesn't actually share the interest. But she had so much on it?'_ Simon looked up nervously. _'That might be the problem though, that I went on her computer without her permission. Worse, I investigated a part of her she wanted nothing more than to keep secret from others. Just about the worst thing a boyfriend can do.'_ Frowning in disappointment at himself Simon picked up his phone and went to message Jeanette just as Alvin entered the room.

"Hey Simon, do you still need to borrow my car?" Alvin asked seeing Simon on the couch.

"Your car? Yeah, I could still use it. The bus stop is a half mile away from the museum where I'm taking Jeanette, but aren't you taking Brittany to the movies?" Simon inquired to his brother.

"I was yeah. Still might be but we'll walk if that happens. I get the feeling though there's been a change of plans and I won't need my car." Alvin said with a smirk on his face. "The catch is, I want the treehouse tonight."

Simon's eyes narrowed in suspicion. "What do you mean you want the treehouse?"

"Come on Si, do I really need to spell it out for you?" Alvin said with a slight mocking edge. "All six of us are young, going out on dates late at night, Dave and Miss Miller are both out of town…"

Simon's face turned red at Alvin's words, all the worse because he was right. "Okay, okay you made your point. Why do you think I'd want the treehouse though?"

"Because the two of you seem to end all your dates up there maybe?" Alvin asked raising his eyebrow at his brother. "I figure its more of a Jeanette thing, but you should still be able to steer her towards your bedroom I bet. And I'm sure Theodore and Eleanor will go to the girl's house because its closer and they have all the picnic stuff. So, none of us will be stepping on anyone's toes." Alvin explained.

Simon was surprised that he couldn't argue against Alvin's logic. "Why Alvin, did you actually plan this night out? I'm impressed." He mocked.

"To be perfectly frank with you Si, something happened today that I want to talk to Brittany about and I get the feeling the treehouse will give us the most privacy," Alvin said seriously, not meeting his brother's challenge. "I learned something interesting about her but I don't know… but I really shouldn't be talking about it before I talk to her. Point is, you can have my car and I get the treehouse. Deal?" Alvin asked holding up his keys.

"Deal" Simon replied catching them as Alvin tossed them to him. "Alvin, I just want you to know if you hurt Brittany then…."

"If I hurt Brittany Si, none of you will hate me more than I would hate myself. So take what you were about to say and shove it." Alvin cut him off in anger before storming towards the back door.

' _Well, that was interesting.'_ Simon thought intrigued before suddenly overtaken by fear? _'Could Brittany have sent him the video and he saw me in It? No, no if Alvin had seen me there's no way he would have given me his car. That would be the least of my worries.'_ He realized. Looking back down at his phone Simon realized that he had less than an hour before he was supposed to pick up Jeanette. _'If she's gone this long without messaging me then it can almost certainly wait.'_ Simon decided, knowledge of his privacy that night bolstering his confidence.

Getting off the couch he began to walk towards his room. _'Still, no reason not to look my best for the exhibit.'_ He thought mentally choosing his outfit.

Jeanette was going crazy. She felt full in a way she had never felt before and it was not necessarily unpleasant. But every single little movement caused the toys inside her to change positions, rubbing against her spots and each other inside her.

Jeanette had spent nearly the entire afternoon cleaning her room. Later when Theodore was done with the cheesecake she had insisted on washing the dishes just to keep herself away from the enveloped key. Consciously she knew there was no reason not to use it. Simon hadn't told her not too and she was definitely horny enough to do it. But there was still something inside her that wouldn't let her use it, that seemed to scream at her that she hadn't earned it.

So instead she did her best to distract herself. She was currently having a problem selecting an outfit for her date tonight. _'A dress would be most appropriate, but which one?'_ She thought to herself. Brittany had insisted that Jeanette "diversify her wardrobe" a few months earlier so she had several different options. Eventually, she settled on a simple purple dress that had a loop secured around her neck tied to the back of the dress. It hugged her chest before flowing out past her waist leaving her arms and most of her back bare.

Looking at herself from every angle, Jeanette couldn't see any evidence of the belt beneath her dress, and she was reasonably confident that even if anyone did it would be mistaken for underwear. Grabbing the envelope, Jeanette walked downstairs, where she ran into Brittany who had just finished frowning at her phone. Looking up at her sister her eye's widened.

"Ooh la la, where are you and Simon going where you need to look so fancy?" Brittany asked after nodding approvingly at her sister.

"Just an event at the museum, the project we were a part of in school gave us contact with some sponsors who expressed interest in our work and… You don't really care do you?" Jeanette smiled at her sister seeing the blank look covering her face.

"Not really no," Brittany replied. "I got the gist of it; you and Simon are going to a fancy dance and I get to go in the treehouse. Alvin better have a homemade candlelit dinner up there or I'm going to be pissed." Brittany said irritably.

"The treehouse? Why does he want the treehouse?" Jeanette asked in confusion.

"I don't know, he wouldn't tell me, said we'd talk about it tonight. Given that you're wearing that though it probably is a good thing, be a shame to get such a pretty dress dirty in the treehouse." Brittany said shrugging her shoulders and gesturing to Jeanette. "Of course, for all I know Simon might rip it off you as soon as you get home." She said smirking.

' _Oh, I hope so.'_ Jeanette thought to herself blushing. "I… I don't know what you mean." She replied.

"Oh puh-lease, you and Simon aren't as subtle as you think you are when you just 'happen' to go into the treehouse after every one of your dates." Brittany said teasing her sister. "Just so you know, Eleanor already left with Theodore for their picnic, so they won't be back for a while, chances are they will come back here so you and Simon will have the time to take the dress off properly in his room."

Opening her mouth to respond to Brittany's taunt Jeanette was cut off by a knocking at the front door.

"That's probably Simon," Brittany said looking down at her phone. "And Alvin chooses now to ask me to come to the treehouse. I guess I'm off, have fun tonight Jeanette." Brittany says walking away.

"You too!" Jeanette calls after her. Jeanette's heart was beating like a drum in her chest as she went over to the door. Opening it she was met by Simon's sharp intake of breath.

"Wow." Simon said, his mouth hanging open. Jeanette's heart soared, direct compliments on her appearance from Simon were rare. He simply preferred to compliment her mind instead. Still, it was nice to be admired.

"You like it? It isn't too much?" Jeanette asked while examining Simon's own outfit. It consisted of a simple dark blue suit with a lighter blue undershirt.

"You look great." Simon said quickly in response smiling at Jeanette before a slight lip quiver. "Ahh, is that the _only_ thing you're wearing?" he asked with a slight catch in his voice betraying his nervousness.

Jeanette blushed fiercely at the implication behind his question. With a shaking hand, she held out the envelope to Simon. Looking down at it he sighed and began to speak slightly disappointed and rehearsed. "Look Jeanette, I only really left a letter because I thought it would make you more comfortable. I completely understand if you don't want to do it for real but…"

"it's the key Simon." Jeanette said hurriedly, her facing turning an even darker shade of red. "I never took the key out, and I've had… _it_ , on all day." She said squirming slightly, the toys inside her rubbing against each other.

Simon's face contorted in a puzzled expression before the meaning of her words registered in his mind. "Oh. OH!" He said opened-mouthed as the realization dawned on him and he grabbed the envelope. "Let me see." He demanded as a wolfish grin broke out on his face.

Hearing Simon's commanding words Jeanette felt herself become even wetter than the low levels she had been dealing with all day. Grabbing the sides of her dress Jeanette slowly began pulling it up, revealing more and more of her legs until finally the belt was entirely revealed.

Simon dropped to one knee and felt at the belt ensuring it held firm and wasn't overly tight. He felt a surge of pride at his invention given that, to his knowledge, it was the first chipmunk chastity belt even invented. _She's wearing it, she's actually wearing it and she gave me the key.'_ He thought wildly. Running his fingers down her crotch her soon felt the hooks of the vibrator and butt plug latched into place on the belt. A light tap on the toys caused Jeanette to let out a light moan in pleasure. _'Going to have fun with those later.'_ Simon thought grinning even wider.

He continued to explore his belt, ensuring that everything was in its place for several minutes until he felt a breeze blow into the house from behind him. Jeanette let out a quiet yelp as she felt the same breeze before her face returned to a deep scarlet.

' _I just flashed the street for five minutes straight while Simon touched me'_ Jeanette thought shuddering to herself in arousal. His hands had felt so skilled and precise, as they always did, even though the belt. Simon predicted and found the pleasure paths across Jeanette's skin, tracing them all over her body and driving her mad in the process. Him doing so while she was belted almost caused her to collapse right there.

Simon stood up and looked Jeanette in the eye, his eyes nearly as wide as hers in the same realization. "You can put the dress back down now." He said before crushing her lips in a passionate kiss.

Jeanette dropped her dress and returned the kiss equally passionate. She soon felt the hardness of Simon's length beneath his pants as he slowly rubbed himself against her. "God, you're amazing Jeanette." He growled in her ear. "Its taking all of my willpower not to throw you to your knees right now, but if I do I doubt we'll ever make it to the party. Now let's go, the sooner we get there, the sooner we can leave." Simon said pulling Jeanette by her hand to Alvin's car sitting in the street.

Jeanette stumbled over her long dress, there was a reason she didn't wear them that often! But nonetheless, she followed Simon without complaint wondering what he had in store for her. On the way to the museum, Simon could barely keep his eyes on the road. _'Does she realize what she does to me?'_ He wondered as she looked at her smiling. Stopping at a red-light Simon sighed and turned to Jeanette. "I suppose we should cover some ground rules, shouldn't we?" Simon asked, worried about her expectations. Jeanette returned his gaze.

"Maybe… Maybe later. If we decide to keep this going. For tonight, I think I'd rather leave it up to you. I trust you Simon." Jeanette replied smiling nervously. "Just, nothing too crazy, okay?" She asked.

"Of course! I just wanted to make sure you were going to have a good time and…" Simon trailed off as Jeanette's words weighed on his mind. _'She trusts me. So much that she's wearing a chastity belt I made her and… No, stop it. You can figure that out later.'_ He thought to himself. "Just make sure you let me know if you're uncomfortable, at all." Simon said.

"I will. I promise." Jeanette said. They continued their way to the museum finally reaching it shortly before the event was set to begin. Simon got out and helped Jeanette out of her seat, taking her hand like a gentleman and escorting her to the entrance. They hand barely made it to the side walk before Simon pulled her aside.

"I completely forgot to test this." Simon said excitedly as he pulled out his phone.

' _Test what?'_ Jeanette thought right before the vibrator inside her began to buzz unexpectedly causing Jeanette to moan loudly before it stopped as abruptly as it started. _'That apparently.'_ She thought to herself as she recovered.

Adjusting the settings Simon grinned at her. "That was a bit stronger than what will probably be usual tonight, but I thought I'd give you a little taste before we went inside." He said casually. "Try not to let anybody on to the fact that you're walking around stuffed with toys."

' _Fat chance of that!'_ Jeanette thought to herself. She hadn't quite expected that burst of vibration, but she was getting soaked in anticipation of being teased even more. "I'll try." She said meekly, unconvinced of her own acting ability.

"You better if you want me to take that belt off when we get home." Simon said threateningly. _'I have no intention of leaving it on her of course.'_ He reassured himself. _'But it will be fun to watch her squirm.'_

Jeanette's eyes widened at Simon's words, but she relaxed a little when she saw the amused glint in his eye as he took her arm. Deciding not to call his bluff, Jeanette let him walk her into the entrance hall of the museum.

The event wasn't anything major and didn't truly involve either of them, Simon and Jeanette had been invited after impressing a member of the museum's board who thought they would enjoy some of the exhibits. As they walked around and spoke to some of the other guests Simon would periodically cause the vibrator inside Jeanette to buzz making her suck in deep breaths or pause in mid-sentence, but no one seemed to suspect anything was off.

In between these conversations, Simon's hands would wander over Jeanette. Sliding down her back and gripping her rear, pulling her against him, massaging her shoulders, but never long enough to be considered improper. Near the end of the night, Simon and Jeanette found themselves speaking with the member of the board who had invited them.

"Mr. Seville! Miss Miller! How good to see you this evening, are you enjoying yourselves?" He asked politely.

' _More than you know.'_ Jeanette thought to herself, as she clenched herself around the toy in her core. Making small talk with the board member soon proved to as boring as she had feared but her and Simon nodded along politely. Suddenly, a mischievous glint appeared in Simon's eyes that Jeanette more often associated with Alvin.

"Excuse me, I need to use the restroom." Simon said, interrupting the board member. Leaning over he gave Jeanette a peck on the cheek after whispering in her ear "wait here." As Simon walked away the board member continued his one-sided conversation while Jeanette wondered what Simon was planning.

She got her answer a moment later as the toy inside her began to vibrate, but not the entire toy as it had before, but rather only at the base. Jeanette managed to successfully suppress her urge to moan, easier in fact than she did before. Still confused she was startled and wasn't entirely able to suppress her yelp of surprise when the vibrating sensation began to move its way up the toy. It did so smoothly and slowly until reaching the top when it began moving equally smoothly down, Jeanette began to breathe heavier as she realized what it was supposed to mimic. The function slowly began to increase in both speed and vibration as Jeanette felt herself getting flushed.

Simon's sudden voice behind her made her jump. "Sorry, about that." He said, grinning and deliberately ignoring Jeanette's mortified expression. "Excuse me sir, didn't you tell us about that project in graduate school? I'd like to hear that story again please." Simon asked the board member.

"Certainly! I'm surprised you remember it, though it is an amusing tale I suppose." He said as he began the story in question. Jeanette remembered the story as well, it had taken him almost half an hour to tell before. _'At the rate, the vibrator is increasing I don't think I'll make it that long.'_ Jeanette thought to herself.

As the story wore on, the toy continued its simulated thrusting. The speed increased so that by 10 minutes in Jeanette could barely count the time in between the top vibrating and the bottom. Simon continued to pretend to listen to the story while smirking at Jeanette out of the corner of his eye. Jeanette began to sway her hips, eager for any kind of additional stimulation. Her face grew beet red and her breathing became heavy. Jeanette was lost in a world of pleasure as the toy inside her pulsed, eventually, she was brought out of her stupor by the board member.

"Miss Miller? Are you okay my dear? You look a bit faint." He asked. Simon stood slightly behind him, phone out while he adjusted the settings slightly smirking confidently at her.

"I… uh… I think… I'm just not feeling well, I'm going to go get some air." Jeanette said distractedly. Immediately Simon's smile fell away, replaced with a look of concern. Rushing out of the museum Jeanette soon felt a cool breeze on her hot skin. Walking towards the car she soon was on the side of the building and sat down on the grass against the wall and groaned in frustration as she realized Simon had turned the vibrator off. Sliding her hands up her legs she tried in vain to elicit any kind of feeling from her fingers to her core. She felt herself clench hard around the toy inside her desperate for the pleasuring she had been feeling just a minute earlier.

Simon soon excused himself after disabling the vibrator. Walking with an urgency in his step he made his way to the door. _'I shouldn't have pushed her so much.'_ He thought worriedly to himself. _'I was so busy making her squirm I must not have seen her trying to get my attention…'_ Turning around the corner he saw Jeanette sitting in the grass groaning. "Jeanette, I am so sorry. I didn't mean to…"

"Simon. Pleeeeease! Turn it back on!" Jeanette begged as she heard him. Turning to her side she looked Simon in the eyes, desperately trying to stimulate herself through the belt. "I need it, I'll do anything please just turn it back on." She moaned. Simon simply looked at her. Jeanette's dress was hiked up so far, he could clearly see the belt. Juices clearly leaked out through the sides showing just how aroused Jeanette was.

' _She's absolutely loving this!'_ Simon thought to himself excitedly.

"What do you want Simon? A blowjob like you said earlier? Pleeeease just stick your cock in my mouth!" Jeanette begged as she closed her eyes, focusing on herself. "I'll swallow everything! Just let me _Hmghf!_ " Jeanette let out a muffled squeaked as Simon roughly pulled her mouth around his member.

"If you insist." Simon said releasing his hold on Jeanette's head. Soon Jeanette was bobbing her head up and down on Simon's shaft. Running her tongue over the underside she lightly sucked on his tip causing him to let out a low moan of pleasure. "That's it Jeanette." Simon said, acting on instinct he was running his hand from the top of Jeanette's forehead through her hair to the back of her head, driving Jeanette wild. "That's a good girl. Take it a little deeper. Fuuuuck yes." Simon moaned as Jeanette forced herself to take more and more of him in her mouth.

All too soon Simon felt himself reaching his limit. "That's a good girl Jeanette, I'm almost there, I'm about to cum Jeanette, remember what you said and drink in all!" He said shooting his load in Jeanette's mouth. Jeanette swallowed every spurt as it shot out, slowly savoring the musky, salty taste. At last Simon was spent and Jeanette slowly licked the last of his cum from his tip.

Simon looked down at Jeanette who looked up at him. Her focus on herself had faded while she did her best to bring Simon to orgasm, but the need hadn't disappeared. Merely taken a backseat to her desire to please her lover. Simon looked up and looked around, straining his ears to hear anyone around. Satisfied that no one was nearby he looked back down to Jeanette. Taking out his phone he turned the vibrator back on with its thrusting function. However, he set the vibration settings as low as it could go and the thrusting speed as slow as possible. Jeanette began to shudder as she felt the toy begin to tease her.

"You asked me to turn it back on, you didn't ask for the same settings," Simon said smirking at his girlfriend quivering on the ground. "Now come on, we're going home," Simon said as he helped Jeanette to her feet enjoying the feeling of her pressing against him. _When we get there, I am going to do my best you feel like a puddle of pleasure.'_ Simon thought to himself as he got in the driver's seat.

As they drove back home Jeanette was lightly humping at the air, trying anything to increase the pleasure torturing her. The toy within her still buzzed slowly. _'Is he trying to drive me crazy?'_ Jeanette wondered while letting out a whimper.

After what felt like hours, they made it back to Simon's house. Pulling into the driveway Simon noticed that the door to the Chipette's house was slightly ajar. Based on the sounds coming from inside he had a pretty good Idea why. Turning to Jeanette he said, "I'm going to go shut that door, I want you in my room, on my bed, as naked as you can be facing towards the wall with the door open."

Nodding weakly Jeanette began to walk towards the house, swaying with each step as she tried to control herself. Half crawling up the stairs she finally made it to Simon's room. Slowly she pulled off her dress, the feeling of it moving past her skin when combined with the buzzing device inside her was almost too much.

Soon she was on all fours facing the window, her belt still wrapped itself around her hips as she unconsciously wriggled her ass at the door behind her. Through the window, she could see Alvin and Brittany having sex in the treehouse. Though she was still too far away to see any detail, the sight nonetheless caused her imagination to run wild.

While Jeanette was lost in thought Simon entered the room and admired the view of his girlfriend's ass, swaying back and forth. Realizing she hadn't noticed him come in Simon surprised Jeanette with a firm slap to her ass. Hearing her moan in pleasure Simon grinned wolfishly. He had already removed his shirt and bent over to growl in Jeanette's ear "Keep your hands right there, I am going to take the belt off, but if you try to touch yourself, you will regret it."

When Jeanette moaned her consent, Simon stepped back. Slowly, he noisily pulled the key out of the folded envelope. Stepping forwards yet again, Simon traced the key up Jeanette's leg teasing her even more, sliding it around her hips, he drew little circles around the hidden pocket where the padlock was hidden.

Sliding it out Simon unlocked the belt and pulled it off slowly. It come off, pulling the toys out with a pop! As soon as it was off Simon was hit by the deep, musky, slightly sweet smell that emanated from Jeanette's slightly gaping hole. She dripped onto the sheets beneath her, gripping the sheets below, unknowingly extending her claws and tearing the sheets in a struggle to keep herself from touching her aching clit.

Simon was instantly harder than steel and realized that Jeanette didn't need any more teasing or foreplay. Grabbing her hips, he shoved himself in stretching her out around himself. Jeanette moaned in absolute pleasuring nearly reaching her climax from the insertion alone. Simon quickly began thrusting hard and fast. Jeanette signaled her agreement with wordless whimpers of pleasure. She had been teased all day and she was more than willing for this.

Simon for his part was feeling mad with power. _'I did this to her.'_ He thought in absolute desire, _'I made her want me this bad. I am going to make her mine. Give her the reward for her hard work today.'_ Increasing the speed of his thrusts he felt his climax coming soon. Bending over he whispered in Jeanette's ear. "Cum." Was his simple, yet firm, demand,

Jeanette's eyes rolled in her head, she opened her mouth letting out a long drawn out moan. She clenched hard around Simon's shaft milking him, desperate for his cum. Feeling Jeanette's spasms, Simon soon reached his own climax, unloading himself into Jeanette.

Both chipmunks panted with exhaustion before collapsing in Simon's bed. Laying down on his back, Jeanette soon laid her head on his chest while Simon slowly ran his hand across her head. "We need to wash the belt before we do that again," Jeanette mumbled as sleep began to take hold.

"It can just go in the washing machine," Simon said bemused, but Jeanette had already fallen asleep. Smiling, Simon closed his eyes and allowed his own exhaustion to overtake him.

* * *

 _ **AN: Wow, when I said, "A little longer" I swear I wasn't thinking "Twice as long". Still, I felt like I needed the extra thousand words or so to set up the next couple chapters, which is funny because the next few chapters (5-8) are just to set it up so I can write pointless smut instead of plotty smut. This is getting a lot more plotty than I anticipated but I like it.**_

 _ **I am going to try, no guarantees, but try to release at least one chapter a week.**_

 _ **I hope this chapter read a little smoother than the previous one. Reviews and criticisms are more than welcome and thank you for reading.**_


	5. Date Night Chapter 3

Alvin let out a long sigh as he heard Britany's footsteps coming up the stairs to the treehouse. _'Okay brain, I waited until she's here. Now what?'_ He thought jokingly to himself. Alvin had spent the entire day thinking about this conversation, but he had avoided thinking about what he was going to say, mostly because he was afraid he would mess it up. Instead, he had chosen to trust his instincts.

When Britany finally entered the treehouse living room she looked around before raising an eyebrow at Alvin. "No candles, no dinner, no suit, and you didn't do anything with me for the last two Fridays. You're on thin ice Alvin, what's your plan tonight and why did you call me up here?" She asked, a warning edge to her voice.

"Do you seriously think that I would wear a suit and not tell you to wear a dress?" Alvin responded. "Or try cooking something more than ramen noodles? No matter how many candles you light I don't think that's going to be your kind of romantic."

"You still haven't answered my question Alvin, what's the plan tonight?" Brittany asked ignoring Alvin's barb. She walked over to the couch and sat down.

"Well originally I was planning on taking you to the movies," Alvin began "but then I watched a short movie today that I liked." He said also walking over to the couch and sitting down next to Brittany who once again raised an eyebrow at him. "Now, you're the one who's trying to be an actress, so you know all the proper words and stuff. Basically, this movie has terrible camerawork, but I thought the lines were good and it has an interesting twist." Alvin said pulling out his phone.

"So let me get this straight, Instead of going to the movies we're going to watch a low budget short film on your phone?" Brittany asked disbelievingly.

"Tell you what Brit, if you don't like the video we can still go see the movie. I just wanted to talk to you about it." Alvin said as he pulled the video Brittany had sent him up.

'This better be some movie." Brittany said under her breath. As she watched Alvin was able to pull up the video scooting closer, he put his hand around Brittany's shoulder as the video loaded. Brittany kept a slightly annoyed look on her face but couldn't help smiling inside. She couldn't deny she liked being close to Alvin. As the video pulled up however a look of horror came on her face as she saw it on Alvin's phone screen wearing a much different expression.

Unable to say anything, Brittany felt her cheeks flush with embarrassment as she saw first her own naked body on screen then heard own words. _'Oh my god, it sounds like something out of a bad porno!'_ She thought to herself in humiliation. Continuing to watch the video she became aware of two things. First, Alvin hadn't moved his arm in any way. Not to make a move nor to pull away from her. Second, she was getting wet.

Squirming slightly in her seat, Brittany felt Alvin pull her closer as if to reassure her. As the video got to the point where she began talking about Simon, Brittany couldn't take it anymore. "Okay! You've made your point Alvin! What do you want?" She practically screamed as Alvin paused the video.

"Funnily enough that's where I came when I watched it this afternoon," Alvin replied calmly ignoring Brittany's outburst. "I had no idea you wanted to try anal Brit. I figured bringing it up at this point would be a one-way ticket to slapsville to be honest."

"I… I like the idea," Brittany admitted. Deciding to change course she tried to go on the attack. "Where'd you even get the video?" She asked harshly.

"Oh, you know, I used my super-secret hacking skills to search your phone to find it. You sent it to me dummy, I guess you didn't mean too?" Alvin asked unsurprised.

"No! I'm not… I just… I didn't… I am not a slut!" She exclaimed at Alvin as she felt herself get even wetter from the mixture of humiliation and loss of control of the situation.

A look of surprise came over Alvin's face. "Hold on Brit, you think this video makes you a slut? That it makes me think you're a slut?" He asked incredulously. Seeing Brittany's lack of reaction, he began to laugh. "Brit that is… hahaha… that's not… hahahaha!"

"It's not funny Alvin!" Brittany shouted at her boyfriend. Still unable to see the humor in the situation. "It's not normal to do that! To want that!"

"What? It's not normal to want to feel sexy?" Alvin retorted between giggles. "It's not normal to want your boyfriend to want you? Or is it wanting sex that's not normal?" He challenged gaining control of himself.

Infuriated by Alvin's caviler attitude Brittany felt a wellspring of emotions and desire well up inside her "It's being a successful, famous, independent woman and wanting to be 'put in my place' or 'be your bitch' that isn't normal Alvin!" Brittany shouted using finger quotes. "Its filming dozens of videos of myself masturbating to masturbate to the thought of sending them to you that isn't normal!" She raged. Standing in front of an opened-mouth Alvin and seeing the complete shock in his face caused much of the anger Brittany felt to dissipate, replaced by shame. _'He wasn't trying to hurt me'_ she thought. "It's feeling worthless because I couldn't even get my boyfriend to cum when we first had sex that isn't normal."

Taken aback at Brittany's outburst Alvin felt suddenly way out of his depth. _'I thought this was just a little kink of her's '_ He thought to himself shocked. Getting to his feet, Alvin walked over to Brittany and wrapped his arms around her and pulling her tight against him. "Listen Brit, I'm not going to lie. The idea of you _voluntarily_ doing what I say is one of the hottest things I can imagine, and its _because_ you're a successful, famous, independent woman that it's so hot." He explained. "Those are the reasons I fell in love with you, if you weren't those, you wouldn't be you. Making those videos, that's just a kink you have, there's nothing wrong with it." Alvin continued to try and convince Brittany.

Taking a deep breath Alvin continued. "As to our first night, Brit that was all on me." He started. "I… I got way too horny and I wasn't thinking, and I ended up hurting you. Even if it was just a little I felt terrible, so I had a little trouble focusing." Alvin said apologetically. "But it wasn't anything you did, god Brittany you felt amazing that night…" Alvin trailed off, remembering the night.

' _What? Hurt me? When?'_ Brittany thought completely confused.

"I threw you on the bed and you hit your head," Alvin said, lost in thought. "I heard the thunk as you hit the wall and I felt terrible. I had gotten too carried away, I was thinking with the wrong head." His hand began to snake down Brittany's side where it pressed just under the waistband of her pants.

Brittany struggled to remember what Alvin was describing, she could only remember the excitement she felt. The eager anticipation of what she had been dreaming of for years. Brittany remembered being thrown on the bed, it was hitting her head she couldn't remember. _'Obviously, it wasn't very painful.'_ She thought to herself before gasping in surprise.

"Oh, looks like you liked watching that video with me Brit," Alvin said as he slipped his paw into Brittany's panties, feeling her slippery lips. "Or maybe you're remembering that night? I had so much I wanted to do to you." He said as he nuzzled Brittany's neck causing her to let out a long moan. "So much I still want to do to you."

' _Oh god, please just do it.'_ Brittany thought to herself as she melted because of Alvin's expert touch. _'I want you to make me your bitch Alvin, I already told you that in the video.'_ Opening her mouth to say something similar, Brittany's eyes widened as she felt Alvin put his free hand over her mouth.

"Shhh, let me finish Brittany. If you wanted me to stop you would have said so by now." Alvin whispered in her ear. "I regretted hurting you more than you can imagine, and I was so worried that you would reject me if I told you what I really wanted. But now I know the truth about how you feel." He said as he began to circle her clit making Brittany squirm against him. "Now I know just what you want, you want _this_ don't you?" Alvin asked as he pulled Brittany's rear against his erect cock through their clothes.

Brittany tightened her grip on Alvin's arms as she pressed herself against him. Letting out a low whimper and moving his hand from her mouth she began to beg. "Alvin please, the video, the memories, your fingers, pleeeeease! I need this!" _'I need you'_ She thought to herself as her mind was clouded by lust.

"You need it huh?" Alvin asked. Brittany could hear the smirk on his face as she began to rub herself against him unconsciously. "Need what Brit? I'm going to need you to spell it out for me." He said teasingly.

"I need your cock," Brittany whined catching herself and Alvin by surprise. "I need you inside me, I need you to fuck me, I need to feel you fucking me until I can't think straight!" She began to pant as Alvin's touch brought her closer and closer to release. "Please Alvin, just fuck me already!" Brittany screamed.

Alvin was harder than he had ever been in his life. The most beautiful girl he had ever met was literally begging him to fuck her. There was a part of him that was practically dying to fulfill her wish. _'But where would the fun be there?'_ Alvin thought to himself. Slipping a finger inside Brittany's folds he relished the sound of her moan before he whispered in her ear. "No. Be happy I'm inside you at all right now." Alvin began to curl and straighten his finger as he nipped lightly at Brittany's ear. "You say you want to be put in your place, but I think you already know where that is. On your knees in front of me naked." He growled.

Brittany was panting as she humped herself against Alvin's finger. Hearing the commanding tone in his voice she knew that he was right. Suddenly, Alvin's finger curled inside her rubbing right against her G-spot causing Brittany to let out a long moan as she came.

Alvin grinned as felt Brittany clench around his finger in the throes of her orgasm. Soon after she was leaning against him for support as he pulled his hand out of her now cum soaked underwear and brought it to her mouth. "Clean it," Alvin ordered as he pushed his finger against her lips.

' _How did he know?'_ Brittany thought to herself as she wrapped her lips around Alvin's finger. Brittany had long fantasized of Alvin forcing her to clean her juices off him and the idea of finally doing so made her take to her task with vigor. Brittany sucked lightly on his finger, rubbing her tongue around his digit lapping away all traces of her juices enjoying the taste.

Alvin used his free hand to begin to pull down Brittany's pants, something to which she did was glad to help with. After she had kicked off her pants and panties, Alvin went to work attempting to unhook her bra with a single hand. A trick that he accomplished on the first try causing Brittany to smile in her task as he slipped her bra off from under her shirt and threw it to the side.

Soon Alvin pulled his finger out of Brittany's mouth with a slight popping sound. "That's enough, now lose the shirt." He ordered, stepping away from Brittany. Alvin was amazed his jeans hadn't burst a seam from how much he was straining against them. Watching as Brittany followed his command and removed her shirt she seemed acutely aware of her nakedness as a blush made its way up her cheeks. Still, she made no move to cover herself and looked Alvin in the eye wondering what he had planned next.

Alvin smiled at the beautiful sight before him. He never got tired of seeing Brittany naked. Letting his eyes wander up and down noting that Brittany's thighs still gleamed. Striding over to her he soon stood right in front as she met his eyes.

Amazingly he was still thinking semi-clearly, "I love you Brittany and I don't want to hurt you, at least not for real." Alvin whispered. "So I want you to promise me if you want to stop you let me know. Understood?"

Brittany shivered at Alvin's words. "I promise." She whispered back as her heart pounded in her ears. Smiling that same cocky smile that drove her crazy, both good and bad, Alvin put his hands on her shoulders and began to push down lightly.

"Well, I think you know where you want to be now, don't you?" Alvin asked as Brittany dropped to her knees in front of him.

Looking at Alvin's cock, Brittany's eyes were wide with excitement. She had seen him before of course, but being so close, with him standing above her controlling her through her own desires, Brittany felt like she was on fire as she slowly licked his tip.

Alvin shuddered as Brittany began her work on him. _'This is amazing.'_ He thought to himself. He had felt her mouth around him before of course, but never like this. Standing above Brittany he had his hands in her hair gripping lightly as she lightly bobbed on his cock, taking him deeper and deeper with each push. Alvin applied no pressure to force her lower, she did so on her own wanting to prove she could.

Brittany quickly succeeded forced Alvin's cock entirely down her throat. Her eyes began to water as she kept herself down, fighting her instincts. Brittany rubbed her tongue along the underside of Alvin's manhood. Looking up she could barely make out the outline of Alvin's face as he looked down at her.

All too soon Alvin pulled Brittany off him. Brittany gasped and began coughing even as she was leaking like a faucet, more than ready to feel him inside her. When Brittany had recovered Alvin growled at her "Turn around and get on your hands and knees". Quickly moving to obey Brittany pointed her rear at Alvin, her tail lightly circling to help her stay steady.

Alvin soon lined himself up with Brittany's entrance, he had felt himself getting dangerously close to cumming before but he knew how to tease Britany. Rubbing lightly against her entrance Alvin heard Brittany begin to moan at his teasing. "This is as far as I'm going Brit. If you want to fuck me, you better slide back." Alvin said, he was barely able to react in time as Brittany did push back sliding his cock down slightly so that instead of filling her he slid between her lower lips causing her to groan.

"Alvin please…" Brittany said stretching out her pleading. This was the best and worst feeling she had ever felt. Alvin was so close, but he wouldn't just slip in her. She felt him pulsing against her, getting coated in her juices as she rocked slightly against him. Her whole body tensed up when she felt one of Alvin's fingers prod against her asshole.

"This is the one hole you have that I haven't fucked yet," Alvin said as he pressed his finger against her. He doubted they would get to anal tonight, but she clearly liked to have it played with. "When I do, I'll have fucked the whole set, get it?" He said beginning to chuckle before noticing Brittany lying face down and reaching back behind her.

' _Am I really about to do this?'_ Brittany thought to herself as she grabbed each one of her cheeks. _'Oh god, I am. I am about to do this.'_ Spreading her cheeks apart she caused her asshole to stretch ever so slightly open. "Please," Brittany whispered.

For the second time that night Alvin was speechless. He had long fantasized about this but to actually be about to do it was… unbelievable. "Britt I…" He began

"Please Alvin! Fuck my ass!" Britany practically shouted. "I have thought about it for years, played with it for years, I even fucking masturbated with it this morning. Now I am literally begging you Alvin, please just fuck my ass!"

Alvin was momentarily shocked before taking his cock and lining it up with her puckered hole. Thinking about asking her again, Alvin shook his head and instead leaned in her ear, "If you want it so bad, do it yourself" He whispered.

Brittany groaned and began to push herself back, slowly forcing Alvin's cock down her ass she felt herself stretch obscenely. Soon she felt herself push against Alvin's waist and stopped while she caught her breath. _'He's in my ass'_ She thought to herself in a haze, _'I finally have Alvin… in my ass.'_ Brittany savored the feeling. It was different, and not necessarily better than in her pussy but definitely not much worse.

Soon, Alvin began to pull back. The feeling of Brittany was different, it felt tighter at her entrance but looser elsewhere. His thrust slowly picked up pace and Brittany was pushing herself against him. The two were quickly rutting with all their energy.

Brittany was still face down and quickly felt her orgasm approaching. Every thrust stimulated spots she didn't even know she had. But what triggered her climax was Alvin gripping a handful of hair and pulling her head up as he slammed into her one last time. Brittany felt her knees buckle as her second orgasm of the night rocked her body. Alvin's cock spurted rope after rope of cum inside her ass which soon began to leak as he let her go and she slumped down in exhaustion.

Brittany could barely move as the aftershocks of her orgasm rocked her body. She was aware of Alvin leaving before coming back with a blanket. Laying down next to her Alvin draped the blanket around them both and held Brittany against him. "Wow." Was all Alvin could say.

"I'm sorry," Brittany said in response.

"I.. What?" Alvin asked clearly confused. "Don't be, that was amazing." He said, trying to cheer her up completely unaware of what could make her apologize.

"Not for this!" Brittany says, slightly indignant. "I meant, for thinking of Simon In the video," Brittany says embarrassed. "I don't… I mean… I'm happy with you." She finished grabbing his arm tight against her chest.

Alvin grinned behind her. "Don't be, unless we're apologizing for every time we thought of each other's siblings in a sexual way, then we'll be here a while." He said trying to interject some humor. "Let's just go to bed, we'll sit down and talk about this tomorrow.

"You might sit down. I doubt I will, did you need to be so rough?" Brittany asks as she begins to drift off to sleep.

"Oh, you loved it," Alvin responded, equally tired. "Now I've fucked the..."

"If you make that terrible pun again, I will kick you out," Brittany said

' _You are so bluffing._ ' Alvin thought as he drifted off to sleep. Pulling Brittany closer his last conscious thought was _'I doubt you could even walk right now.'_

* * *

 **Author's note: I fully intended to post this in Septemberer and have a whole witty joke about misspelling "month" as "week" in my last author note but that doesn't really work now does it?**

 **More seriously, I am sure this chapter is a letdown after that wait but now date night is over and the plot advances.**

 **I didn't realize how much life decided it was going to throw at me as soon as I started school. So now, I am cautiously estimating one chapter every month on average. That should give me two months to catch up.**

 **As always, reviews and criticism are welcome.**


	6. A Steamy Summer Storm Chapter 1

Jeannette walked down the stairs to Simon's lab in the basement, the now familiar feeling of the belt sealed around her waist though she lacked the plugs today. The day before Simon had gone down and begun to work on an experiment, the details of which he hadn't shared with either of his brothers _'though_ _I have a pretty good idea.'_ Jeanette thought to herself.

Before last Friday whenever she and Simon had been intimate, they had made sure to not to risk her getting pregnant. That night's series of events, however, had left them both so clouded with lust that neither of them had thought to take such a precaution until the day after.

After a thorough cleaning, more for a psychological benefit than a physical one, and several tests, Jeanette was reasonably confident that she was not going to end up pregnant. _'Yet anyway'_ she thought with a smile. Still, she couldn't deny how amazing the feeling had been and it seemed Simon had agreed.

As she opened the door to his lab, Jeannette saw Simon sealing a bottle of a sweet-smelling opaque orange liquid. "What's that Simon?" She asked.

Jumping slightly at the unexpected noise, Simon turned to Jeannette. "Hey Jeanette, I didn't see you there." He said when he noticed her. "I'm just working on an experiment, if it works it will provide a superior method of contraception with no major long-term side effects." He explained, slightly shaking the container.

"Really?" Jeanette questioned. "There's no way even you developed something like that in a week." She doubted.

"No, but I didn't have to. It is based on an old formula created by a could of doctors in the seventies." Simon conceded. "It's called the Plote-DeVise formula. It works by essentially turning the entirety of the seminal tract in males and fallopian tubes in females toxic to both sperm and egg cells." He explained turning back to look at the cages of lab mice on the wall. "It was dropped because the amount of chemical needed to coat the linings in most creatures, including humans, is enough to poison them. However, chipmunks metabolize the chemical quickly enough that it poses little risk to them in doses effective enough work for its contraceptive effects." Simon continued. Turning back to Jeanette he began to walk towards the stairs saying. "This is the latest version of the formula, it needs to chill before it can be used but the side effects should be at least halved."

"Side effects?" Jeanette said as she followed him up the stairs. "What kind of side effects?"

"Increased hormone and pheromone production. The metabolizing process of the toxin releases them at an increased rate, effectively increasing libido and arousal." Simon answered as he turned towards the kitchen. "That's why I had the mice in separate cages, otherwise they just don't stop." Reaching the fridge, Simon put the container on the bottom shelf, next to a gallon of milk and an over half-empty bottle of orange juice. "I hope Theodore and Eleanor get back home before the storm hits," Simon said absentmindedly. "They went grocery shopping for this weekend, right?" He asked turning back to Jeanette.

"I think so," Jeanette replied. Looking down a coy smile appeared on her face. "One last question about the formula Simon, Is it airborne or is that just from me?"

Simon, having seen her eyes and smile, grinned. "Little of column A, little of Column B. Either way you're going to take care of it now aren't you?" He asked while unzipping his pants. "After all, Alvin and Brittany are at your house right now."

"Well it that case…" Jeanette said as she dropped to her knees in front of him. "I better get to work."

Running her tongue from the base of Simon's cock to the tip, Jeanette wrapped her lips around his head. Grabbing the top of her head, Simon began to unconsciously rub his hand through her hair. "Good girl Jeanette… ohhh, I haven't had any relief all day. You're going to fix that for me huh?" Simon moaned as Jeanette swirled her tongue around his head.

As Simon was lost in the pleasures of Jeanette's tongue a crack of thunder seemed to almost shake the house. "Wow, they really better get home soon or else they will be in a downpour," Simon said. Jeanette however, was occupied and couldn't respond.

* * *

Brittany moaned as her fingers danced along her clit, teasing herself slowly towards an orgasm. But she wasn't just trying to cum this time, she was putting on a show. Alvin stood at the foot of her bed, recording her with his phone. Brittany knew that he would probably use it on lonely nights but she had the suspicion Alvin wanted it for more abstract reasons. He simply wanted videos of her doing he said because just having those videos made him feel strong. And Brittany was too happy to oblige.

"Alvinnnn…" She moaned writhing on the bed, edging closer and closer and closer. "Alvin this feels so good." Brittany was lost in a fog of pleasure and failed to notice Alvin walking closer and closer to her until he was right above her legs.

It would be an awkward place to give her oral, but Alvin had a different idea anyway. Leaning over he held his breath, as Brittany's own quickened. Finally, her ministrations exposed her clit fully to the air and in that exact moment, Alvin blew a quick breath on it, as though he was blowing out a candle.

Brittany's body, already on the brink and hypersensitive, exploded in pleasure. "Alvinnnnnnnn!" She screamed in orgasmic bliss, her whole-body convulsing. At the same moment, a crack of thunder shook the windows and caused Alvin to jump in surprise.

"Damn, I knew I was good but I didn't realize I was that good!" He said after a moment.

"Oh… shut up, Alvin… I did most of the work." Britany retorted out of breath. A few drops of rain fell on her from her open window.

"Maybe, but I bet it wouldn't have been so thunderous without my help," Alvin said in response. "Anyway, as much fun as I've had here, I'm going to go back to my house and clean up my room. You can pay me back tonight when you're there with me."

After groaning at Alvin's pun Brittany waved a hand at Alvin and asked, "Can you shut my window before you go?"

After doing as she asked, Alvin quickly walked around the girl's house making sure all the doors and windows were shut. The storm they were going to get that night was supposed to be pretty bad and last all weekend so the girls were staying over at their house, Simon had rigged several backup power sources and a couple of downloaded movies meant they would have a fun little sleep in.

After spending several minutes securing their house, Alvin left and ran home. The rain was already coming down hard. Rushing inside Alvin quickly removed his shoes and walked to the kitchen to make himself something to eat.

Checking the fridge he saw the nearly empty bottle of orange juice, drinking the entire bottle he felt momentarily guilty before noticing the second bottle. _'Ah, that must be a new bottle'_ He thought, throwing the old bottle of orange juice in the garbage. _'I wonder if Theodore will get an extra on accident then?'_ He wondered Idly as he walked upstairs to his room.

* * *

Eleanor let out an involuntary moan as one of Theodore's fingers curled inside her hitting her G-Spot. Luckily a loud rumble of thunder echoed nearly at the same time so the only person who heard her was Theodore himself.

"Quiet now Ellie," He whispered in her ear, "Or do you want them to catch us?" He said, uncurling his finger. Catching herself this time, Eleanor squirmed in Theodore's touch. Ever since last Friday he had been so much more physical with her. He barely kept his hands off her when they were alone, and even in public, he could be brazen.

As he was proving now. They were at the store buying some last minute groceries for the weekend before the hit, they had grabbed most of their list but as Eleanor was looking for one of their last items Theodore had slipped his hand between her legs, teasing her. Hidden on one side by a stocking cart and on the other by a wall they were fairly well hidden, but far from unreachable.

"We… ah… we should probably get going Theo." Eleanor managed to stumble out as Theodore fingered her. "We can finish this t-tonight if w-we wait too much longer… ohhhh… we might get caught in the worst of the storm, and we still haven't gotten orange juice or... Ohhh!" She yelped as Theodore found a particularly sensitive spot.

"You're right Eleanor," Theodore said reluctantly withdrawing his hand from between her legs. "Wouldn't want you getting wet, would we?" He asked wistfully.

Hearing the serious tone in his voice Eleanor couldn't suppress a giggle. "It's a bit late for that Theodore, thanks to you." Theodore looked at her confused for a moment before he realized what she meant as a blush spread over his face. _'He's so cute when he does that'_ Eleanor thought lovingly. _'He hasn't changed at all since last week, I almost thought he might. I feel like I have.'_ Struck by a sudden thought Eleanor grinned. Turning her head to make sure there was no one else nearby Eleanor spoke up. "But you know, there's no point in wearing wet clothes," She said seductively.

Theodore's jaw dropped as Eleanor Squatted and removed her panties. Walking pass Theodore she hid them in the pocket of his hoody. On an Impulse she winked at him and began to walk towards the registers with their groceries, her hips swaying just enough to show her now lacking attire.

Eleanor saw Theodore walk out of the store as she was paying. Walking out her yelp was cut off as she turned the corner and Theodore kissed her. Holding her for nearly a minute his hands wandered to her now bare rear and Eleanor shivered as the cool wind from the storm blew on her bare skin.

Finally breaking off the kiss, Theodore growled in her ear, "You are going to pay for that tonight."

"I can't wait," Eleanor whispered back.

* * *

Later that night, all six chipmunks were sitting in the Seville living room about to watch a movie. The power had gone out on the street a few minutes earlier but Simon's backup power supplied them with just enough energy to keep the lights on and keep appliances working. Everything was fine until the computer fried.

"What do you mean you lost it?" Brittany demanded hands placed on her hips standing right behind Simon. "You said you downloaded the movies this morning?"

"I did, and I put them on this flash drive," Simon replied still fiddling with the computer near the TV. "But apparently the one time I don't safely eject it, it lost all the data. And the internet is out so I can't even redownload the movie. "

"See Si, this is why you just take it out every time. Then it gets used to it and doesn't break when you need it." Alvin spoke as though he was offering wise advice.

"That is definitely not how it works Alvin," Jeanette responded from the couch. Shifting slightly to get in a more comfortable position with the belt hidden around her waist.

"Can you fix it, Simon?" Theodore asked, his attention split between the conversation going on in the living room, and Eleanor making them fruit smoothies in the kitchen. Her lack of underwear was apparent through the tight pajama pants she was wearing.

"If I could access the internet and reset it from the backup in the cloud sure. But with the storm, the cable is out and so is our internet." Simon replied standing up.

"Well that's great, what do we do now?" Brittany asked.

"Play a board game?" Suggested Jeanette

"I don't think we have all the pieces to any of our board games," Theodore said as Eleanor entered the room.

"Here's your smoothies everyone," she said carrying a cookie sheet as a makeshift platter with six large glasses of a yellow-orange liquid. You guys didn't have enough oranges, so I cheated a little and used orange juice." She explained as she passed them out.

"I'm sure its great Eleanor, when's the last time you made something bad?" Simon asked as he took a glass.

Taking a deep drink, Alvin burped and grinned. "Taste fine to me." He said after he was finished, earning a disapproving glance from Brittany.

As everyone took a glass and began to drink, the conversation once again turned to entertainment for the night.

"So no movie, no cable, no board games, is there anything we can do for fun tonight?" Brittany asked as she looked around as though hoping entertainment would appear from the air. She wiggled slightly on the floor, a slight heat building in her core. _'Am I imagining it or is it starting to smell really good in here?'_ she wondered sipping from her glass of Eleanor's smoothie.

"What, do I not count?" Alvin asked with mock indignation. Taking another drink from his glass as he did so. "These are seriously good Eleanor." He said as he finished the glass.

Slightly startled by Alvin's compliment Eleanor began to thank him when she was interrupted by Brittany. "Well Alvin, I was thinking of something all of us could do. Plus it would help if it was something that takes longer than two minutes." She retorted. Causing Jeanette to choke on her drink as she started to laugh.

Raising one eyebrow up Alvin looked at Brittany before glancing at Simon, who was helping Jeanette to clean up, and then back at Brittany _'Do you really want to play this game Brit?'_ He wondered.

Brittany saw his looked and interpreted it correctly, her cheeks reddening before she looked down. _'Well that was strange'_ Eleanor thought as she noticed the exchange. Shifting slightly to find a position that wasn't so awkward, she was far more turned on by not wearing any panties in front of everyone than she thought she would be. Picking up her now nearly empty glass the drank the rest of the smoothie and began to refill it.

"Anyway…" Simon said after Jeanette had finished her coughing fit. "We will just have to hope the internet comes back on and find something to d… and activity to do until then." Shifting his pants slightly to hide his growing erection, _'Jeanette smelled so good…_ ' he thought.

"Well that doesn't leave many options," Jeanette said from next to him wriggling her hips slightly. Something about having Simon on top of her with everyone else in the room was making her squirm, the unforgiving belt, however, did not offer any comfort. "How about a trivia game?" she offered.

"What, and let you and Simon have all the fun? Pass." Alvin answered quickly. He couldn't deny that something was turning him on but he had no clue what. "How about truth or dare instead? Here…" Picking up the TV remote Alvin spun it on the table until it stopped with the power button pointing directly at Eleanor. "You get to ask first Eleanor, unless someone else has an idea?"

Theodore, on his third glass of Eleanor's smoothie, grinned as he thought of a way to get back at her for the grocery store earlier. "I think that sounds like fun Alvin." He said as he walked towards the table.

"Uhh, okay," Eleanor said, looking she decided to satisfy her curiosity from last week. "Simon, Truth or dare?" she asked.

"Truth" Simon replied,

"What was the present you brought over to our house for Jeanette last Friday? Eleanor asked.

Simon and Jeanette's faces both went red almost immediately. Simon reached for his barely touched glass and took a drink to buy himself time to answer, _'Why did that have to be the first question?'_ He thought. Thinking quickly, he almost had a satisfactory answer when he heard Jeanette answer next to him.

"He built me a… he built me a chastity belt." Jeanette said her face flushed red, though whether that was embarrassment or arousal she couldn't tell. Setting her now empty drink glass down she tried to sit up straight as she poured herself another, feeling a familiar wetness begin to form between her legs.

Alvin raised an eyebrow at the statement, he had figured Jeanette probably liked something crazy just like everyone, but he hadn't suspected that or that Simon would be into it.

Brittany's eyes blinked back and forth between Jeanette and Simon. A part of her idly wondered if Jeanette was wearing the belt right now and if Simon could build a second one. She felt a heat between her legs as she tried to cross them. Sipping from her now second glass of smoothie to cover it up, but that almost seemed to make it worse.

Theodore's eyes went wide as he heard Jeanette answer the question, he couldn't help but think what it would be like to have control over when Jeanette could cum or even just touch herself. Theodore began to wonder what it would be like to sleep with Jeanette.

Eleanor, to her credit, was embarrassed about asking her question. She had thought it had been something cheesy or corny, not something so private. "Uhh, sorry Simon." She said lamely as an apology.

"It's not your fault, you didn't know," Simon said after a moment's hesitation. Deciding just to play along with the game he turned to Brittany and asked, "Truth or dare?"

"After that kind of a question started us off, I don't know which is safer." Brittany joked. "truth," she said after wiggling for a moment.

Simon wracked his brain trying to figure out an appropriate challenge for Brittany to perform, each one raunchier than the last. Suddenly Brittany's glass fell over soaking her pants. She quickly took them off, not noticing the small stain appearing between her legs. Unbidden, images from last Friday popped in his head and he found he had his question. "How would you describe Alvin in bed?"

Brittany looked at Simon surprised, she hadn't expected him to escalate the questions. Still, she was bound to answer it and it's not like she could say anything bad. "Well for one what I said earlier was completely lie, he can actually last for two and a half minutes." She began eliciting a laugh. "But seriously, he's amazing he has a kind of natural confidence that makes you want to do what he asks you to and… its really almost indescribable." She finished lamely

Sitting down on the floor cross-legged, Brittany looked around noticing Eleanor's eyes were staring at Alvin in curiosity. Finally, her eyes settled on Jeanette. Unable to contain her curiosity she asked "Jeanette, truth or dare?"

Jeanette could see the gleam in Brittany's eyes and knew what her dare or question would be. Still, the idea made her squirm. After giving Simon a side-eyed look, she answered, "Dare I guess".

Brittany's face broke out in a broad grin as she gave Jeanette her dare. "Show us all every feature of your chastity belt on the belt itself."

"Hold on second." Simon interrupted, setting down his barely touched drink "That's a very personal thing to ask her to do and I get that we're trying to have fun but…"

"It's okay Simon," Jeanette said cutting Simon off. "I… I want to show them." Simon looked back at her and saw that not all, and possibly not most of the blood in her face was from embarrassment.

"If you're sure Jeanette." He said reluctantly sitting back dawn and sipping his drink.

Jeanette drank down her entire second glass before she finally wriggled out of her pants to show off her belt. Her audience watched in faces ranging from curiosity in Brittany to clearly visible arousal in Theodore. Sitting back down, Jeanette saw how much attention Theodore was paying to her and quickly asked him "Truth or dare Theo?"

Deciding to get it done with quickly because he had a plan, Theodore finished his fourth glass of smoothie before answering "Truth."

"Uhhh, when was the first time you had sex with Ellie?" Jeanette asked, a cloud of lust beginning to cloud her thoughts.

Simon looked at Jeanette in amazement, that wasn't the kind of question he had expected from her at all. _'What is going on with her, is she really getting that aroused just from showing off her belt?_ ' he wondered.

Theodore had expected to answer right away, but even in his lust filled state he knew that this question didn't just affect him. Glancing sideways at Eleanor she gave him a little nod. Taking that as approval, Theodore answered: "Last Friday, I was too nervous to try anything before that." He said simply. "Eleanor, truth or dare?" He asked quickly turning to his girlfriend who was just finishing her own third glass of smoothie.

Taken a bit by surprise, Eleanor's eyes narrowed she mentally weighed likely questions against the likely dares before finally answering "Dare."

Grinning broadly, Theodore stepped backward and slightly off to the side so that he was facing everyone. Looking back up at Eleanor he said: "It doesn't seem fair that both your sisters are out of their pants so I dare you, to walk up to me and take your pants off and then grab your ankles for ten seconds." He ordered, letting a bit of the controlling voice he sometimes used during sex slip out.

This dare caused everyone in the room to gasp if Jeanette's question was startling Theodore's was a complete surprise. Eleanor began to blush furiously as she walked up to Theodore. Finally, with agonizing slowness she began to slide her tight leggings down her legs, exposing her shapely rear to the four munks behind her. When she had gotten home, she had taken a quick shower but decided to leave the underwear off as a way of teasing Theodore. She wasn't quite sure if she regretted that now or not.

When her pants were all the way off, she bent over and grabbed her ankles giving everyone behind her a completely unobstructed view of her now glistening slit. After seeing this, The perfect idea popped into Alvin's scheming mind. Reaching a count of ten at last she turned to go sit back on the couch. When she did so she felt Theodore kiss her cheek before sitting down next to her.

"Well, that was a pleasant view," Alvin said, breaking the silence. "And I think I'm the only one who hasn't been asked yet."

"Fine Alvin, truth or dare?" Eleanor asked hastily already having a plan to get back at Alvin for starting the game in the first place.

"Dare," Alvin said confidently.

"Strip all the way naked," Eleanor demanded smugly, thinking that Alvin would embarrass himself trying to weasel his way out of it.

Instead, Alvin just stood and shrugged his shoulders, asking, "Am I making this a show or do just want to see me naked?"

"Just strip Alvin," Eleanor said, desperate not to be the only one naked.

Sensing her discomfort Alvin chuckled and slowly began to strip, over exaggerating everything except taking off his underwear, which he did quickly. Afterward, he stood proud, even all five of the people in front of them stared at a fully erect cock.

Rotating his hips from side to side he finally got to ask his own question. "Theodore, assuming Eleanor was okay with it and so was Simon, would you sleep with Jeanette?" He asked, not bothering asking truth or dare.

"I…Uhh…. What kind of question is that? Theodore asked in shock.

"A serious one, would you?" Alvin insisted.

"I.. well… yeah, I guess. But ONLY if Simon and Eleanor were both aware and okay with it." Theodore stressed, looking between his brother and his girlfriend uncertainly.

"Thanks, Theodore, for the record, I would too," Jeanette said. With a sheepish grin, mirroring Theodore's uncertain look as she glanced at Simon and Eleanor.

Hearing this, Alvin's face broke out in a triumphant grin. "So it's settled then, we are all trading partners tonight?"

* * *

 **AN: Well that was fun to write as always feedback is appreciated.**

 **AN2: It took way to long to clean this up a little, and it probably still has enough errors to make an editor pull their hair out.**


	7. A Steamy Summer Storm Chapter 2

"What?" exclaimed Simon and Brittany simultaneously, even as Jeanette blushed and Theodore's eyes furrowed in thought. Eleanor however, barely heard his words slightly distracted by Alvin's subtle hip turns.

"I said, we are trading partners tonight. Jeanette and Theodore just admitted they want too, Eleanor's eyes are glued to my cock, and you two are crazy if you don't have a thing for each other." Alvin said smugly, certain that this was the truth, though careful not to say exactly why he knew. That was up to Brittany to say.

Britany opened her mouth to respond that no, she certainly did not have a "thing" for Simon before realizing just how stupid that would sound considering the video evidence Alvin had on his phone. That shut her mouth abruptly as her face blushed, both with that fact and that she hadn't yet heard Simon refute Alvin's claim.

Simon's face was red as well, as soon as Alvin mentioned him and Brittany Simon's thoughts had turned to the show she had unknowingly given the other day. He would be lying if he said he hadn't let his eyes follow her when she was in a swimsuit even before then, and he certainly had thoughts before when he was alone in bed. Shaking his head he went to respond more firmly when he realized Brittany hadn't yet said anything. Could she really be attracted to him?

After hearing Alvin's declaration Theodore's eyes lit up at the idea. Of course, he had thought of Eleanor's sisters before, and Jeannette was sexy in a reserved kind of way. At least compared to her sisters. Still, this wasn't a decision that was all his. Leaning over he whispered in Eleanor's ear. "Are you alright with this?"

Eleanor blushed furiously as she heard Theodore's question. The truth was she was currently fighting an internal battle of wills against the part of her that was screaming that it was wrong to want to fuck Alvin, he was Brittany's boyfriend, Theodore's brother, hell he was practically like an older brother to her _without_ those two. And yet she could feel that part of her slowly losing against the rising tide of lust that reminded her of what Brittany had said about Alvin in bed, of all the times Alvin had outperformed her in sports (conveniently forgetting about all the times Eleanor had outperformed him), and most of all how fucking horny she was and how there was a nice big cock not five feet away. When Theodore asked his question Eleanor realized she had a way that she could get it, all she would need to do is let her boyfriend plow her sister. That would be so bad right? Theodore wouldn't hurt her, Jeanette would probably love it.

"I… if you are," Eleanor said tentatively. Theodore turned her head, forcing her to break eye contact with Alvin's member, before kissing her deeply, showing all his love and passion in that movement.

"You better believe I am," Theodore said. Standing up he looked over at Jeannette who looked away quickly and squirmed. Theodore thought he saw traces of wetness on her thighs right around the belt. Smiling slightly, he spoke up. "Sounds like fun to me Alvin, I'm perfectly okay with it. **IF** Everyone else is too."

"Thank you Theodore. See you guys, Theodore is fine with it and it's his girlfriend I'm going to screw. That really just leaves you two, are you really that disgusted by each other? He asked, trying to provoke a rise out of them. He had a feeling that the more they thought about it the less chance there was of them going for it. In truth, he agreed with Theodore, this was an all or nothing event. If he couldn't get them to agree it wasn't happening.

Simon and Brittany continued to struggle with their natural resistance to the idea, but even as they both tried to draw up reasons to disagree their minds were filled with ideas and curiosity about each other. And the growing sense of arousal that came from neither one rejecting the idea yet. Seeing their struggle, Jeannette made up her mind. "Do it you guys. I've seen you checking each other out and if you don't do it now, you'll always be wondering." She said, even as she glanced over at Theodore, her own thoughts racing.

Hearing Jeanette's words, the last blocks of resistance feel inside of Simon as he finally said "If… If you guys are really okay with it then… yes, I want to."

Hearing Simon's declaration, Brittany couldn't deny anymore that she wanted this too. Sighing dramatically, she responded. "Fine, let's do it. Go have fun with Ellie Alvin." She said dismissively even as she began to crawl over to Simon.

Raising his eyebrow at Brittany's attitude, Alvin made sure to grab her ass as he walked by towards Eleanor. "Just remember who this belongs too Si. I'm just letting you borrow it for the night." Walking towards Eleanor, he saw Theodore, seemingly startled by the rapid change in attitude smile as he got up and walked towards Jeanette. Not standing in front of Eleanor he grinned. "My eyes are up here you know." He said mockingly.

"I've made my choice," Eleanor said with a small smile, even as she licked her lips.

"Well since you're down their anyway, why don't you put that smart mouth to better use?" Alvin said as he rested his hand on top of Eleanor's head. "Or would you rather skip the foreplay and get right to the main event?

"Afraid you won't be able to last?" Eleanor asked teasingly, looking up at Alvin even as she smiled and drew her tongue along the base of his shaft. Alvin's quick-witted reply was lost in the moan he let out at her action. Taking that as a go ahead, Eleanor slowly began to envelop the head of his cock in her mouth. Running her tongue in small circles around the tip, she licked a drop of pre-cum as it dripped out, savoring the taste.

The truth was that Eleanor didn't get to do this that often. Theodore had always been concerned that she was feeling good when they were intimate, and even as rough as he had become in the last week, he was rather impatient. He wanted her wet so he could fuck her senseless, he saw blowjobs as a waste of time otherwise.

' _But Alvin seems to love them…'_ Eleanor thought to herself. She felt him apply the slightest bit of pressure, so little she wasn't certain she was even really feeling it but she knew what he wanted. Without even realizing it, she was taking him deeper and deeper. Alvin was just a little longer than Theodore, maybe half an inch, but he wasn't quite as girthy, slipping down her throat easier. As she did so she heard Alvin groan, "Fuuuuck. That's right Eleanor, swallow my cock. Swallow it like a good b… Swallow it nice and deep." He said stumbling over his words trying not to push his luck.

Hearing his stumble, Eleanor pulled herself off Alvin's cock, bringing one hand up she began to stroke it even as she kept her face underneath it. "You were about to call me a bitch weren't you Alvin? About to tell me to swallow your cock like a good bitch?" Eleanor asked before licking at one of Alvin's balls, nuzzling the underside of his shaft causing Alvin to let out more moans of pleasure.

"Is that what you call Brittany in bed? Do you call my sister a bitch?" Eleanor asked in between licks. "Do you make her get on her knees and suck your balls just like I am right now? What else have you made her do? Has she…"

"Shut up and suck my cock, or I'll show you what happens when you aren't being a good bitch," Alvin growled from deep in his chest, all thought of restraint in his words gone.

Eleanor almost came from Alvin's tone alone. She shuddered at his command and found herself parting her lips as she went to fulfill his command when she stopped, overcome with an incredible, if foolish, desire to see what happened if she taunted him one more time. "Why? What are you going to… Mmmmph!" Eleanor grunted as Alvin's grip on her head, previously so light suddenly became as hard as steel as he forced her down his shift completely until his balls hung underneath her chin.

Completely surprised Eleanor found herself growing even wetter. Struggling to breathe she looked up at Alvin, tears beginning to well in her eyes even as she felt his grip loosen. "Stay." He ordered, before letting his hand fall away. Eleanor never even thought to disobey this time, staying where she was even as her body screamed her need for oxygen. Gagging around Alvin's cock, Eleanor tried to blink away the tears in her eyes, doing her best to stimulate Alvin even as he remained still. Finally, just when she felt like she couldn't take it anymore she felt Alvin tug her hair back, pulling her off of his member with an audible pop. As she collapsed on the couch gasping for air, her ass sticking up high revealing her dripping slit Eleanor thought for sure Alvin was going to fuck her now. She needed it, she craved his dominance over her. Looking over her shoulder, she saw Alvin standing over her, his muscular frame seemed to tower, his face haloed by the light above. Eleanor shivered in delight, turning her head waiting for the expected next move.

Instead, however, she felt Alvin sit on the couch next to her. Abruptly he grabbed her legs and pulled her across his lap. Yelping in surprise, Eleanor felt his munkhood tip pressed against her stomach. Her tail flapped wildly around, her shapely rear and soaked cunt on full display. "Alvin what are you do…EEE!" Eleanor yelped again as she felt Alvin's hand land hard across her asscheek.

"You didn't finish your job. This is your punishment." Alvin said a sadistic smile on his face. " _This_ is what happens when you aren't a good bitch." Before bringing his hand down on her other cheek. Causing Eleanor to yelp again. _'How is this so much different from when Theodore does it?_ She thought to herself. Of course, Theodore had never spanked her like this, it was always when he was already inside her during their fucking. This, this was different. Alvin brought his hand down once more, switching sides again. "Start counting, I'm thinking 20 is fair." He said, slapping her ass once again.

"Four," Eleanor said, trying to stifle a moan.

"Now you're just being a dumb bitch, since when do you start counting from four?" Alvin asked mockingly as he spanked her once again.

"One," Eleanor grunted, her ass was starting to get red from Alvin's assault, but she felt her juices running down her thigh and knew that making him stop was out of the question. Eleanor continued to count as Alvin spanked, alternating between her cheeks as he did. Eleanor was so preoccupied with counting and keeping herself under control that she failed to notice Alvin slowly lessening the force behind his slaps, making sure that the pleasure always outweighed the pain. "Twenty… four" Eleanor managed to pant out, feeling like she was right on the verge of orgasm, with just a little push she thought she would fall. _'Is this what Jeannette feels like all the time with that belt on?'_ She thought, looking over and her sister, who was currently convulsing along Theodore's cock. With her attention distracted by that sight, she failed to notice Alvin's change in target.

Bringing his hand down hard once again, this time Alvin aimed between her legs, striking her firm on her labia lips, the entire force of the slap vibrating across her body into her clit and G-spot simultaneously. Letting out a scream that was half pain and all pleasure, Eleanor felt herself cum hard. Almost as hard as she had that night with Theodore just a few days earlier. As the waves of pleasure rocked through and left her in a numbed daze, Eleanor barely realized what was happening as Alvin seemed to lift her up, righting her so that she was sitting on his lap and rising even more, until she almost came a second time as Alvin brought her down on his cock.

Eleanor let out a shaky breath as she felt Alvin thrust into her still sensitive core, drilling deep. It felt as though a receding wave was only building into a tsunami inside Eleanor and Alvin's roaming hands did nothing to quell it. One slid her shirt off before grabbing and massaging her tit even as the other reached down between her legs, drawing little half circles around her clit, teasing the hypersensitive nub.

Alvin felt himself fast approaching his limit and was determined to make Eleanor cum alongside him again. Eleanor's amazing mouth earlier had brought him almost to the edge and her wriggling on top of him hadn't let Alvin cool down. As such, he began to thrust his hips up even harder. Driving inside of Eleanor's soaking wet snatch, he felt her beginning to the clench around his cock. Turning the nipple he held in one hand and lightly pinching the clit held between his fingers in the other, Alvin plunged inside of Eleanor, letting loose spurt after spurt of his seed into Eleanor. Soon it was spilling out of Eleanor even as she climaxed around him once more, before falling down off of Alvin and onto the floor.

As both participates sat and caught their breath, they couldn't help but enjoy the show being put on by their siblings. Simon currently had Brittany on the verge of begging to be fucked as he expertly ran his fingers along her body, seemingly pleasuring every spot at once. Jeanette was currently laying on her back, her eyes threatening to roll into the back of her head as Theodore roughly plunged into her, heedless of the cum that already filled her.

' _Theodore'_ Eleanor thought in her lust filled haze. Going to stand, Eleanor's legs refused to hold her, causing her to drop again to her hands and knees. Completely unperturbed, Eleanor crawled over to her boyfriend, desiring only to be close to him when exhaustion overtook her.

* * *

 **AN: Well, that took a while. Initially, I was going to wait and release this scene and the next couple as a single chapter, and I might just end up editing this chapter to put the rest in, but I figured this was a fairly self-contained scene and it was already a decent length, so I decided to post it anyway.**

 **As always criticisms are welcome. However, while I make no promises, I am interested in what pairings and "content" you'd to see in the future. Please, feel free to make suggestions.**


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